Hydrogen cation


Reaction thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: John E. Bartmess

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Reactions 101 to 150

C4H9O- + Hydrogen cation = 1-Propanol, 2-methyl-

By formula: C4H9O- + H+ = C4H10O

Quantity Value Units Method Reference Comment
Δr1567. ± 8.4kJ/molCIDCHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.
Δr1568. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr1539. ± 8.8kJ/molH-TSHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.
Δr1540. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale

C5H11O- + Hydrogen cation = Amylene hydrate

By formula: C5H11O- + H+ = C5H12O

Quantity Value Units Method Reference Comment
Δr1561. ± 8.4kJ/molCIDCHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.
Δr1561. ± 12.kJ/molG+TSBoand, Houriet, et al., 1983gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr1533. ± 8.8kJ/molH-TSHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.
Δr1533. ± 11.kJ/molCIDCBoand, Houriet, et al., 1983gas phase; value altered from reference due to change in acidity scale

C6H13O- + Hydrogen cation = 3-Pentanol, 3-methyl-

By formula: C6H13O- + H+ = C6H14O

Quantity Value Units Method Reference Comment
Δr1556. ± 8.4kJ/molCIDCHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.
Δr1556. ± 12.kJ/molG+TSBoand, Houriet, et al., 1983gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr1528. ± 8.8kJ/molH-TSHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.
Δr1528. ± 11.kJ/molCIDCBoand, Houriet, et al., 1983gas phase; value altered from reference due to change in acidity scale

C3HN2- + Hydrogen cation = Propanedinitrile

By formula: C3HN2- + H+ = C3H2N2

Quantity Value Units Method Reference Comment
Δr1405. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr1406. ± 11.kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Δr1373. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr1373. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase
Δr1376. ± 8.4kJ/molIMRETaft, Abboud, et al., 1988gas phase; Revised: 91TAF

C6H9O- + Hydrogen cation = Cyclohexanone

By formula: C6H9O- + H+ = C6H10O

Quantity Value Units Method Reference Comment
Δr1533. ± 8.4kJ/molD-EABrinkman, Berger, et al., 1993gas phase
Δr1531. ± 9.6kJ/molD-EAZimmerman, Jackson, et al., 1978gas phase
Δr1544. ± 18.kJ/molG+TSBrickhouse and Squires, 1988gas phase; Between acetone, Me2C=NOH
Quantity Value Units Method Reference Comment
Δr1501. ± 9.6kJ/molH-TSBrinkman, Berger, et al., 1993gas phase
Δr1498. ± 11.kJ/molH-TSZimmerman, Jackson, et al., 1978gas phase
Δr1511. ± 17.kJ/molIMRBBrickhouse and Squires, 1988gas phase; Between acetone, Me2C=NOH

H2N- + Hydrogen cation = Ammonia

By formula: H2N- + H+ = H3N

Quantity Value Units Method Reference Comment
Δr1688.0 ± 1.2kJ/molD-EAWickham-Jones, Ervin, et al., 1989gas phase
Δr1688.5 ± 3.3kJ/molG+TSMacKay, Hemsworth, et al., 1976gas phase
Δr1683.2kJ/molN/ACheck, Faust, et al., 2001gas phase; HCrO3(t); ; ΔS(EA)=6.6
Quantity Value Units Method Reference Comment
Δr1656.8 ± 1.6kJ/molH-TSWickham-Jones, Ervin, et al., 1989gas phase
Δr1657.3 ± 2.9kJ/molIMREMacKay, Hemsworth, et al., 1976gas phase
Δr1654.4kJ/molN/ACheck, Faust, et al., 2001gas phase; HCrO3(t); ; ΔS(EA)=6.6

ClO4- + Hydrogen cation = HClO4

By formula: ClO4- + H+ = HClO4

Quantity Value Units Method Reference Comment
Δr1255. ± 24.kJ/molIMRBMeyer and Kass, 2010gas phase
Δr1220. ± 50.kJ/molAcidMarcus, 1987gas phase; Acidity seems too strong by ca. 10 kcal/mol. Other lattice energetics ( Mallouk, Rosenthal, et al., 1984, Finch, Gates, et al., 1977) are also too stable for anions.
Quantity Value Units Method Reference Comment
Δr1200. ± 50.kJ/molH-TSMarcus, 1987gas phase; Acidity seems too strong by ca. 10 kcal/mol. Other lattice energetics ( Mallouk, Rosenthal, et al., 1984, Finch, Gates, et al., 1977) are also too stable for anions.

C7H7O- + Hydrogen cation = Phenol, 3-methyl-

By formula: C7H7O- + H+ = C7H8O

Quantity Value Units Method Reference Comment
Δr1457. ± 5.0kJ/molCIDCAngel and Ervin, 2006gas phase
Δr1462. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr1467. ± 9.6kJ/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Δr1434. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr1438. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase

C6H- + Hydrogen cation = 1,3,5-Hexatriyne

By formula: C6H- + H+ = C6H2

Quantity Value Units Method Reference Comment
Δr1501. ± 21.kJ/molD-EAGarand, Yacovitch, et al., 2010gas phase; Calns says linear H-terminated structure for anion
Δr1486. ± 13.kJ/molG+TSNatterer, Koch, et al., 1994gas phase; Acidity between (Me3Si)2NH and 4-Me-pyrazole
Quantity Value Units Method Reference Comment
Δr1467. ± 21.kJ/molH-TSGarand, Yacovitch, et al., 2010gas phase; Calns says linear H-terminated structure for anion
Δr1452. ± 13.kJ/molIMRBNatterer, Koch, et al., 1994gas phase; Acidity between (Me3Si)2NH and 4-Me-pyrazole

C4H7O- + Hydrogen cation = 2-Butanone

By formula: C4H7O- + H+ = C4H8O

Quantity Value Units Method Reference Comment
Δr1536. ± 12.kJ/molG+TSChyall, Brickhouse, et al., 1994gas phase; Primary and secondary sites are of equal acidity by equilibration. Acidity from Zimmerman, Reed, et al., 1977
Δr1545. ± 10.kJ/molD-EAZimmerman, Reed, et al., 1977gas phase
Quantity Value Units Method Reference Comment
Δr1508. ± 11.kJ/molIMREChyall, Brickhouse, et al., 1994gas phase; Primary and secondary sites are of equal acidity by equilibration. Acidity from Zimmerman, Reed, et al., 1977
Δr1516. ± 11.kJ/molH-TSZimmerman, Reed, et al., 1977gas phase

cyclopentadienide anion + Hydrogen cation = 1,3-Cyclopentadiene

By formula: C5H5- + H+ = C5H6

Quantity Value Units Method Reference Comment
Δr1481. ± 9.2kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Δr1485. ± 12.kJ/molG+TSCumming and Kebarle, 1978gas phase
Δr1495. ± 8.4kJ/molD-EAEngelking and Lineberger, 1977gas phase
Quantity Value Units Method Reference Comment
Δr1455. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Δr1459. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C4H9- + Hydrogen cation = Butane

By formula: C4H9- + H+ = C4H10

Quantity Value Units Method Reference Comment
Δr1739. ± 8.4kJ/molBranDePuy, Gronert, et al., 1989gas phase; The HOF(Et(Me)N.) in Seetula, Russell, et al., 1990 gives BDE(N-H) = 99 kcal/mol, ca. 5 kcal/mol too strong
Δr1745. ± 20.kJ/molBranPeerboom, Rademaker, et al., 1992gas phase
Quantity Value Units Method Reference Comment
Δr1703. ± 8.8kJ/molH-TSDePuy, Gronert, et al., 1989gas phase; The HOF(Et(Me)N.) in Seetula, Russell, et al., 1990 gives BDE(N-H) = 99 kcal/mol, ca. 5 kcal/mol too strong
Δr1709. ± 21.kJ/molH-TSPeerboom, Rademaker, et al., 1992gas phase

C7H15O- + Hydrogen cation = 3-Pentanol, 2,2-dimethyl-

By formula: C7H15O- + H+ = C7H16O

Quantity Value Units Method Reference Comment
Δr1547. ± 8.4kJ/molD-EAMihalick, Gatev, et al., 1996gas phase; Derived BDE: 104.2±2.8 kcal/mol
Δr1548. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr1520. ± 9.2kJ/molH-TSMihalick, Gatev, et al., 1996gas phase; Derived BDE: 104.2±2.8 kcal/mol
Δr1520. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale

HTe- + Hydrogen cation = dihydrogen telluride

By formula: HTe- + H+ = H2Te

Quantity Value Units Method Reference Comment
Δr1385. ± 8.8kJ/molG+TSGal, Maria, et al., 1989gas phase
Δr1386.3 ± 1.7kJ/molD-EAFreidhoff, Snodgrass, et al., 1986gas phase
Δr1393.3kJ/molN/ACheck, Faust, et al., 2001gas phase; ScBr4-.; ; ΔS(EA)=8.4
Quantity Value Units Method Reference Comment
Δr1360. ± 8.4kJ/molIMREGal, Maria, et al., 1989gas phase
Δr1361.2 ± 3.0kJ/molH-TSFreidhoff, Snodgrass, et al., 1986gas phase
Δr1366.9kJ/molN/ACheck, Faust, et al., 2001gas phase; ScBr4-.; ; ΔS(EA)=8.4

C8H7O- + Hydrogen cation = Acetophenone

By formula: C8H7O- + H+ = C8H8O

Quantity Value Units Method Reference Comment
Δr1512. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Δr1515. ± 11.kJ/molD-EAZimmerman, Reed, et al., 1977gas phase
Δr1516. ± 11.kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Δr1483. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Δr1487. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C8H6N- + Hydrogen cation = Indole

By formula: C8H6N- + H+ = C8H7N

Quantity Value Units Method Reference Comment
Δr1472. ± 10.kJ/molTDEqMeot-ner, Liebman, et al., 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.
Δr1461. ± 8.8kJ/molG+TSTaft and Bordwell, 1988gas phase
Quantity Value Units Method Reference Comment
Δr1440. ± 8.4kJ/molTDEqMeot-ner, Liebman, et al., 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.
Δr1431. ± 8.4kJ/molIMRETaft and Bordwell, 1988gas phase

C5H5N2- + Hydrogen cation = 2-Aminopyridine

By formula: C5H5N2- + H+ = C5H6N2

Quantity Value Units Method Reference Comment
Δr1519. ± 10.kJ/molTDEqMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.
Δr1518. ± 8.8kJ/molG+TSTaft and Bordwell, 1988gas phase
Quantity Value Units Method Reference Comment
Δr1489. ± 8.4kJ/molTDEqMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.
Δr1488. ± 8.4kJ/molIMRETaft and Bordwell, 1988gas phase

CH2F3Si- + Hydrogen cation = Silane, trifluoromethyl-

By formula: CH2F3Si- + H+ = CH3F3Si

Quantity Value Units Method Reference Comment
Δr1542. ± 16.kJ/molG+TSAllison and McMahon, 1990gas phase; Between acetone and acetaldehyde. In conflict with Campanaro, Marvin, et al., 1988
Δr1555. ± 19.kJ/molG+TSCampanaro, Marvin, et al., 1988gas phase; Between HF and acetone
Quantity Value Units Method Reference Comment
Δr1508. ± 16.kJ/molIMRBAllison and McMahon, 1990gas phase; Between acetone and acetaldehyde. In conflict with Campanaro, Marvin, et al., 1988
Δr1522. ± 19.kJ/molIMRBCampanaro, Marvin, et al., 1988gas phase; Between HF and acetone

CHF- + Hydrogen cation = CH2F

By formula: CHF- + H+ = CH2F

Quantity Value Units Method Reference Comment
Δr1668. ± 6.3kJ/molG+TSBorn, Ingemann, et al., 1994gas phase; Between EtNH2 and Me2NH
Δr1650. ± 22.kJ/molD-EAGilles, Ervin, et al., 1992gas phase; Triplet state of neutral: 14.9±0.4 kcal/mol higher than singlet
Quantity Value Units Method Reference Comment
Δr1634. ± 5.9kJ/molIMRBBorn, Ingemann, et al., 1994gas phase; Between EtNH2 and Me2NH
Δr1616. ± 22.kJ/molH-TSGilles, Ervin, et al., 1992gas phase; Triplet state of neutral: 14.9±0.4 kcal/mol higher than singlet

indenide anion + Hydrogen cation = Indene

By formula: C9H7- + H+ = C9H8

Quantity Value Units Method Reference Comment
Δr1482. ± 10.kJ/molTDEqMeot-ner, Liebman, et al., 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.
Δr1472. ± 8.8kJ/molG+TSTaft and Bordwell, 1988gas phase
Quantity Value Units Method Reference Comment
Δr1451. ± 8.4kJ/molTDEqMeot-ner, Liebman, et al., 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.
Δr1442. ± 8.4kJ/molIMRETaft and Bordwell, 1988gas phase

C6H3F2- + Hydrogen cation = Benzene, 1,2-difluoro-

By formula: C6H3F2- + H+ = C6H4F2

Quantity Value Units Method Reference Comment
Δr1580. ± 9.2kJ/molG+TSBuker, Nibbering, et al., 1997gas phase
Δr1582. ± 13.kJ/molG+TSBriscese and Riveros, 1975gas phase; Between EtO-, iPrO-; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr1546. ± 8.4kJ/molIMREBuker, Nibbering, et al., 1997gas phase
Δr1547. ± 13.kJ/molIMRBBriscese and Riveros, 1975gas phase; Between EtO-, iPrO-; value altered from reference due to change in acidity scale

C6H4NO2- + Hydrogen cation = Benzene, nitro-

By formula: C6H4NO2- + H+ = C6H5NO2

Quantity Value Units Method Reference Comment
Δr1577. ± 13.kJ/molG+TSCheng and Grabowski, 1989gas phase; between EtOH, iPrOH
Δr1482. ± 13.kJ/molG+TSMeot-ner and Kafafi, 1988gas phase; acidity stronger than all levels of computation by 25 kcal/mol
Quantity Value Units Method Reference Comment
Δr1545. ± 13.kJ/molIMRBCheng and Grabowski, 1989gas phase; between EtOH, iPrOH
Δr1450. ± 13.kJ/molIMRBMeot-ner and Kafafi, 1988gas phase; acidity stronger than all levels of computation by 25 kcal/mol

N3O4- + Hydrogen cation = HN3O4

By formula: N3O4- + H+ = HN3O4

Quantity Value Units Method Reference Comment
Δr1286. ± 30.kJ/molG+TSSchmitt, Krempp, et al., 1992gas phase; Acidity between H2SO4, HNO3..NO3-. Reported: G: 297±7 kcal/mol. Readjusted to newer acidities - JEB; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr1257. ± 29.kJ/molIMRBSchmitt, Krempp, et al., 1992gas phase; Acidity between H2SO4, HNO3..NO3-. Reported: G: 297±7 kcal/mol. Readjusted to newer acidities - JEB; value altered from reference due to change in acidity scale

C3H5O- + Hydrogen cation = 2-Propen-1-ol

By formula: C3H5O- + H+ = C3H6O

Quantity Value Units Method Reference Comment
Δr1563. ± 12.kJ/molG+TSGraul, Schnute, et al., 1990gas phase
Δr1400. ± 50.kJ/molAcidKuhn, Fenzlaff, et al., 1988gas phase; From CH2=CHCH2OH, AP 0.9 eV; est. thermo = 2.5 eV
Δr1409. ± 8.4kJ/molD-EABouby, Compton, et al., 1968gas phase; EA probably 2 eV less
Quantity Value Units Method Reference Comment
Δr1534. ± 12.kJ/molCIDCGraul, Schnute, et al., 1990gas phase
Δr1380. ± 8.8kJ/molH-TSBouby, Compton, et al., 1968gas phase; EA probably 2 eV less

C7H13O- + Hydrogen cation = Cyclohexanol, 2-methyl-, cis-

By formula: C7H13O- + H+ = C7H14O

Quantity Value Units Method Reference Comment
Δr1554. ± 8.4kJ/molCIDCHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.
Δr1551. ± 9.2kJ/molG+TSMajumdar, Clairet, et al., 1992gas phase; Acidity adjusted to 1987 acidity scale
Quantity Value Units Method Reference Comment
Δr1527. ± 8.8kJ/molH-TSHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.
Δr1523. ± 8.8kJ/molCIDCMajumdar, Clairet, et al., 1992gas phase; Acidity adjusted to 1987 acidity scale

C7H13O- + Hydrogen cation = Cyclohexanol, 2-methyl-, trans-

By formula: C7H13O- + H+ = C7H14O

Quantity Value Units Method Reference Comment
Δr1559. ± 8.4kJ/molCIDCHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.
Δr1555. ± 9.2kJ/molG+TSMajumdar, Clairet, et al., 1992gas phase; Acidity adjusted to 1987 acidity scale
Quantity Value Units Method Reference Comment
Δr1531. ± 8.8kJ/molH-TSHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.
Δr1528. ± 8.8kJ/molCIDCMajumdar, Clairet, et al., 1992gas phase; Acidity adjusted to 1987 acidity scale

C7H13O- + Hydrogen cation = Cyclohexanol, 4-methyl-, trans-

By formula: C7H13O- + H+ = C7H14O

Quantity Value Units Method Reference Comment
Δr1563. ± 8.4kJ/molCIDCHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.
Δr1560. ± 9.2kJ/molG+TSMajumdar, Clairet, et al., 1992gas phase; Acidity adjusted to 1987 acidity scale
Quantity Value Units Method Reference Comment
Δr1536. ± 8.8kJ/molH-TSHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.
Δr1532. ± 8.8kJ/molCIDCMajumdar, Clairet, et al., 1992gas phase; Acidity adjusted to 1987 acidity scale

C7H13O- + Hydrogen cation = Cyclohexanol, 4-methyl-, cis-

By formula: C7H13O- + H+ = C7H14O

Quantity Value Units Method Reference Comment
Δr1559. ± 8.4kJ/molCIDCHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.
Δr1555. ± 9.2kJ/molG+TSMajumdar, Clairet, et al., 1992gas phase; Acidity adjusted to 1987 acidity scale
Quantity Value Units Method Reference Comment
Δr1531. ± 8.8kJ/molH-TSHaas and Harrison, 1993gas phase; Both metastable and 50 eV collision energy.
Δr1528. ± 8.8kJ/molCIDCMajumdar, Clairet, et al., 1992gas phase; Acidity adjusted to 1987 acidity scale

HO2- + Hydrogen cation = Hydrogen peroxide

By formula: HO2- + H+ = H2O2

Quantity Value Units Method Reference Comment
Δr1575.3 ± 2.1kJ/molG+TSRamond, Blanksby, et al., 2002gas phase; versus HCCH
Δr1572. ± 8.8kJ/molG+TSBierbaum, Schmidt, et al., 1981gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr1546.0 ± 1.7kJ/molIMRERamond, Blanksby, et al., 2002gas phase; versus HCCH
Δr1542. ± 8.4kJ/molIMREBierbaum, Schmidt, et al., 1981gas phase; value altered from reference due to change in acidity scale

C2F6NO4S2- + Hydrogen cation = C2HF6NO4S2

By formula: C2F6NO4S2- + H+ = C2HF6NO4S2

Quantity Value Units Method Reference Comment
Δr1227. ± 9.6kJ/molG+TSLeito, Raamat, et al., 2009gas phase
Δr1249. ± 9.6kJ/molG+TSKoppel, Koppel, et al., 1998gas phase; corrected from typo in literature: I. Koppel, private Communication, 1998
Quantity Value Units Method Reference Comment
Δr1199. ± 8.4kJ/molIMRELeito, Raamat, et al., 2009gas phase
Δr1221. ± 8.4kJ/molIMREKoppel, Koppel, et al., 1998gas phase; corrected from typo in literature: I. Koppel, private Communication, 1998

C3H4Cl- + Hydrogen cation = Allyl chloride

By formula: C3H4Cl- + H+ = C3H5Cl

Quantity Value Units Method Reference Comment
Δr1590. ± 17.kJ/molG+TSDahlke and Kass, 1991gas phase; Between MeOH, EtOH. Reprotonation site uncertain
Δr1571. ± 8.8kJ/molG+TSPoutsma, Nash, et al., 1997gas phase; Between iPrOH, HF, near tBuOH
Quantity Value Units Method Reference Comment
Δr1559. ± 17.kJ/molIMRBDahlke and Kass, 1991gas phase; Between MeOH, EtOH. Reprotonation site uncertain
Δr1540. ± 8.4kJ/molIMRBPoutsma, Nash, et al., 1997gas phase; Between iPrOH, HF, near tBuOH

C6H4Br- + Hydrogen cation = Benzene, bromo-

By formula: C6H4Br- + H+ = C6H5Br

Quantity Value Units Method Reference Comment
Δr1620. ± 10.kJ/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes
Δr1607. ± 8.8kJ/molG+TSLinnert and Riveros, 1994gas phase; Acidity between quinoline and benzonitrile
Quantity Value Units Method Reference Comment
Δr1586. ± 11.kJ/molH-TSWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes
Δr1572. ± 8.4kJ/molIMRBLinnert and Riveros, 1994gas phase; Acidity between quinoline and benzonitrile

H2NS- + Hydrogen cation = H3NS

By formula: H2NS- + H+ = H3NS

Quantity Value Units Method Reference Comment
Δr1493. ± 13.kJ/molG+TSDePuy and Bierbaum, 1981gas phase; Between CF3CH2OH and H2S, comparable to MeSH; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr1467. ± 13.kJ/molIMRBDePuy and Bierbaum, 1981gas phase; Between CF3CH2OH and H2S, comparable to MeSH; value altered from reference due to change in acidity scale
Δr1480. ± 13.kJ/molIMRBBierbaum, Grabowski, et al., 1984gas phase; NH2- + COS ->.

C2H4FO- + Hydrogen cation = Ethanol, 2-fluoro-

By formula: C2H4FO- + H+ = C2H5FO

Quantity Value Units Method Reference Comment
Δr1553. ± 12.kJ/molG+TSGraul, Schnute, et al., 1990gas phase
Quantity Value Units Method Reference Comment
Δr1525. ± 12.kJ/molCIDCGraul, Schnute, et al., 1990gas phase
Δr1521. ± 15.kJ/molIMRBClair and McMahon, 1980gas phase; Between HF and acetone; value altered from reference due to change in acidity scale
Δr1527. ± 14.kJ/molIMRBDawson and Jennings, 1977gas phase; Between HF and acetone; value altered from reference due to change in acidity scale

C6H3F2- + Hydrogen cation = Benzene, 1,4-difluoro-

By formula: C6H3F2- + H+ = C6H4F2

Quantity Value Units Method Reference Comment
Δr1591. ± 8.8kJ/molG+TSBuker, Nibbering, et al., 1997gas phase
Δr1589. ± 13.kJ/molG+TSBriscese and Riveros, 1975gas phase; < MeOH, <= EtOH; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr1557. ± 8.4kJ/molIMREBuker, Nibbering, et al., 1997gas phase
Δr1555. ± 13.kJ/molIMRBBriscese and Riveros, 1975gas phase; < MeOH, <= EtOH; value altered from reference due to change in acidity scale

C2H5OSi- + Hydrogen cation = dimethyloxosilane

By formula: C2H5OSi- + H+ = C2H6OSi

Quantity Value Units Method Reference Comment
Δr1521. ± 17.kJ/molG+TSDamrauer and Krempp, 1990gas phase; between CF3CH2OH and CH3CHO in acidity
Δr1522. ± 17.kJ/molG+TSFroelicher, Freiser, et al., 1984gas phase; Between aniline, CF3CH2OH in acidity
Quantity Value Units Method Reference Comment
Δr1492. ± 17.kJ/molIMRBDamrauer and Krempp, 1990gas phase; between CF3CH2OH and CH3CHO in acidity
Δr1492. ± 17.kJ/molIMRBFroelicher, Freiser, et al., 1984gas phase; Between aniline, CF3CH2OH in acidity

AlO- + Hydrogen cation = HAlO

By formula: AlO- + H+ = HAlO

Quantity Value Units Method Reference Comment
Δr1539. ± 40.kJ/molD-EADesai, Wu, et al., 1996gas phase
Δr1505. ± 17.kJ/molG+TSDamrauer, Krempp, et al., 1991gas phase; Between CF3CH2OH, pyrrole. Calculations imply that the acid is AlOH, not HAlO
Quantity Value Units Method Reference Comment
Δr1509. ± 41.kJ/molH-TSDesai, Wu, et al., 1996gas phase
Δr1475. ± 17.kJ/molIMRBDamrauer, Krempp, et al., 1991gas phase; Between CF3CH2OH, pyrrole. Calculations imply that the acid is AlOH, not HAlO

Azide anion + Hydrogen cation = Hydrogen azide

By formula: N3- + H+ = HN3

Quantity Value Units Method Reference Comment
Δr1428.8 ± 3.0kJ/molD-EAYang, Kiran, et al., 2004gas phase
Δr1439. ± 13.kJ/molG+TSPellerite, Jackson, et al., 1981gas phase; Acidity near HCO2H
Δr1418. ± 21.kJ/molAcidFranklin, Dibeler, et al., 1958gas phase; From MeN3 and HN3
Quantity Value Units Method Reference Comment
Δr1403.9 ± 3.4kJ/molH-TSYang, Kiran, et al., 2004gas phase
Δr1414. ± 12.kJ/molIMRBPellerite, Jackson, et al., 1981gas phase; Acidity near HCO2H

C2H5N2O- + Hydrogen cation = N-Nitrosodimethylamine

By formula: C2H5N2O- + H+ = C2H6N2O

Quantity Value Units Method Reference Comment
Δr1594. ± 8.8kJ/molG+TSIngemann and Nibbering, 1985gas phase; The experimental dHf(Me2NNO) { Korsunskii, Pepekin, et al., 1967} is incorrect: JEB, manuscript in preparation; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr1564. ± 8.4kJ/molIMREIngemann and Nibbering, 1985gas phase; The experimental dHf(Me2NNO) { Korsunskii, Pepekin, et al., 1967} is incorrect: JEB, manuscript in preparation; value altered from reference due to change in acidity scale

C3H9Ge- + Hydrogen cation = C3H10Ge

By formula: C3H9Ge- + H+ = C3H10Ge

Quantity Value Units Method Reference Comment
Δr1543. ± 8.8kJ/molD-EABrinkman, Salomon, et al., 1995gas phase; D-EA cycle implies BDE(Me3Ge-H) = 80.2
Δr1514. ± 13.kJ/molG+TSBrinkman, Salomon, et al., 1995gas phase; Acidity between mF- and oF-aniline.
Quantity Value Units Method Reference Comment
Δr1512. ± 9.2kJ/molH-TSBrinkman, Salomon, et al., 1995gas phase; D-EA cycle implies BDE(Me3Ge-H) = 80.2
Δr1484. ± 13.kJ/molIMRBBrinkman, Salomon, et al., 1995gas phase; Acidity between mF- and oF-aniline.

C4H7- + Hydrogen cation = 1-Propene, 2-methyl-

By formula: C4H7- + H+ = C4H8

Quantity Value Units Method Reference Comment
Δr1644. ± 7.5kJ/molEndoWenthold, Hu, et al., 1999gas phase
Δr1619. ± 8.4kJ/molD-EAWenthold, Polak, et al., 1996gas phase
Δr1633. ± 9.6kJ/molG+TSBartmess and Burnham, 1984gas phase
Quantity Value Units Method Reference Comment
Δr1613. ± 7.9kJ/molH-TSWenthold, Hu, et al., 1999gas phase
Δr1588. ± 8.8kJ/molH-TSWenthold, Polak, et al., 1996gas phase
Δr1602. ± 9.2kJ/molIMREBartmess and Burnham, 1984gas phase

CHOS- + Hydrogen cation = CH2OS

By formula: CHOS- + H+ = CH2OS

Quantity Value Units Method Reference Comment
Δr1467. ± 13.kJ/molG+TSKass and DePuy, 1985gas phase; This acidity value, and the HOF(HCOSH), appear to have been estimates, and should not be taken as experimental ones - JEB, 2006,G3MP2B3: 334 kcal/mol
Quantity Value Units Method Reference Comment
Δr1435. ± 13.kJ/molIMRBKass and DePuy, 1985gas phase; This acidity value, and the HOF(HCOSH), appear to have been estimates, and should not be taken as experimental ones - JEB, 2006,G3MP2B3: 334 kcal/mol

C2H4NO2- + Hydrogen cation = Glycine

By formula: C2H4NO2- + H+ = C2H5NO2

Quantity Value Units Method Reference Comment
Δr1434. ± 9.2kJ/molCIDCJones, Bernier, et al., 2007gas phase
Δr1429. ± 8.8kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Δr1433. ± 8.8kJ/molG+TSLocke and McIver, 1983gas phase
Δr1410. ± 5.9kJ/molEIAEMuftakhov, Vasil'ev, et al., 1999gas phase
Quantity Value Units Method Reference Comment
Δr1400. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase
Δr1404. ± 8.4kJ/molIMRELocke and McIver, 1983gas phase

C6H3F2- + Hydrogen cation = Benzene, 1,3-difluoro-

By formula: C6H3F2- + H+ = C6H4F2

Quantity Value Units Method Reference Comment
Δr1565. ± 8.8kJ/molG+TSBuker, Nibbering, et al., 1997gas phase
Δr<1575.5 ± 1.3kJ/molG+TSBriscese and Riveros, 1975gas phase; < iPrOH; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr1533. ± 8.4kJ/molIMREBuker, Nibbering, et al., 1997gas phase
Δr<1543.1kJ/molIMRBBriscese and Riveros, 1975gas phase; < iPrOH; value altered from reference due to change in acidity scale

C4H3O- + Hydrogen cation = Furan

By formula: C4H3O- + H+ = C4H4O

Quantity Value Units Method Reference Comment
Δr1636.2 ± 1.5kJ/molG+TSGrabowski and Owusugas phase
Δr1624. ± 13.kJ/molG+TSDePuy, Kass, et al., 1988gas phase; Order:H2O < furan < 2-Me-furan < MeOH. D exchange indicates anion at C-2.
Quantity Value Units Method Reference Comment
Δr1602.1 ± 0.84kJ/molIMREGrabowski and Owusugas phase
Δr1590. ± 13.kJ/molIMRBDePuy, Kass, et al., 1988gas phase; Order:H2O < furan < 2-Me-furan < MeOH. D exchange indicates anion at C-2.

HO- + Hydrogen cation = Water

By formula: HO- + H+ = H2O

Quantity Value Units Method Reference Comment
Δr1633.141 ± 0.042kJ/molD-EASmith, Kim, et al., 1997gas phase; Given: 14741.02(3) cm-1. dHacid(0K) = 389.11±0.014
Δr1622.1kJ/molN/ACheck, Faust, et al., 2001gas phase; MnBr3-; ; ΔS(EA)=1.7
Quantity Value Units Method Reference Comment
Δr1605.57 ± 0.25kJ/molH-TSSmith, Kim, et al., 1997gas phase; Given: 14741.02(3) cm-1. dHacid(0K) = 389.11±0.014
Δr1594.5kJ/molN/ACheck, Faust, et al., 2001gas phase; MnBr3-; ; ΔS(EA)=1.7

C2H2N- + Hydrogen cation = Methyl isocyanide

By formula: C2H2N- + H+ = C2H3N

Quantity Value Units Method Reference Comment
Δr1592. ± 8.8kJ/molG+TSMatimba, Crabbendam, et al., 1992gas phase
Δr1567. ± 8.8kJ/molG+TSFilley, DePuy, et al., 1987gas phase; Matimba, Crabbendam, et al., 1992 indicate that CN- loss interfered with equilibrium here.
Quantity Value Units Method Reference Comment
Δr1561. ± 8.4kJ/molIMREMatimba, Crabbendam, et al., 1992gas phase
Δr1536. ± 8.4kJ/molIMREFilley, DePuy, et al., 1987gas phase; Matimba, Crabbendam, et al., 1992 indicate that CN- loss interfered with equilibrium here.

S- + Hydrogen cation = Mercapto radical

By formula: S- + H+ = HS

Quantity Value Units Method Reference Comment
Δr1465.03 ± 0.29kJ/molD-EABlondel, Chaibi, et al., 2005gas phase; (32)S: 2.0771040(9) eV: revised analysis of Blondel, Delsart, et al., 2001
Δr1465. ± 12.kJ/molEndoRempala and Ervin, 2000gas phase
Quantity Value Units Method Reference Comment
Δr1441.8 ± 0.79kJ/molH-TSBlondel, Chaibi, et al., 2005gas phase; (32)S: 2.0771040(9) eV: revised analysis of Blondel, Delsart, et al., 2001
Δr1442. ± 13.kJ/molH-TSRempala and Ervin, 2000gas phase

imidazolide anion + Hydrogen cation = 1H-Imidazole

By formula: C3H3N2- + H+ = C3H4N2

Quantity Value Units Method Reference Comment
Δr1464.1 ± 3.0kJ/molG+TSGianola, Ichino, et al., 2005gas phase
Δr1465. ± 8.8kJ/molG+TSTaft, Anvia, et al., 1986gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr1433.4 ± 1.7kJ/molIMREGianola, Ichino, et al., 2005gas phase
Δr1434. ± 8.4kJ/molIMRETaft, Anvia, et al., 1986gas phase; value altered from reference due to change in acidity scale

C9H4N3O2- + Hydrogen cation = 4-(Dicyanomethyl)nitrobenzene

By formula: C9H4N3O2- + H+ = C9H5N3O2

Quantity Value Units Method Reference Comment
Δr1277. ± 9.6kJ/molG+TSKoppel, Taft, et al., 1994gas phase; Per Leito, Raamat, et al., 2009, dGacid is likely too weak by at least 1.3 kcal/mol, and possibly 5.3, due to problems in the ladder at dGacid=299
Quantity Value Units Method Reference Comment
Δr1253. ± 8.4kJ/molIMREKoppel, Taft, et al., 1994gas phase; Per Leito, Raamat, et al., 2009, dGacid is likely too weak by at least 1.3 kcal/mol, and possibly 5.3, due to problems in the ladder at dGacid=299

References

Go To: Top, Reaction thermochemistry data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Haas and Harrison, 1993
Haas, M.J.; Harrison, A.G., The Fragmentation of Proton-Bound Cluster Ions and the Gas-Phase Acidities of Alcohols, Int. J. Mass Spectrom. Ion Proc., 1993, 124, 2, 115, https://doi.org/10.1016/0168-1176(93)80003-W . [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Boand, Houriet, et al., 1983
Boand, G.; Houriet, R.; Baumann, T., The gas phase acidity of aliphatic alcohols, J. Am. Chem. Soc., 1983, 105, 2203. [all data]

Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W., Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities, J. Am. Chem. Soc., 1981, 103, 4017. [all data]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]

Taft, Abboud, et al., 1988
Taft, R.W.; Abboud, J.L.M.; Anvia, F.; Berthelot, M.; Fujio, M.; Gal, J.-F.; Headley, A.D.; Henderson, W.G., Regarding the Inherent Dependence of Resonance Effects of Strongly Conjugated Substituents on Electron Demand, J. Am. Chem. Soc., 1988, 110, 6, 1797, https://doi.org/10.1021/ja00214a023 . [all data]

Brinkman, Berger, et al., 1993
Brinkman, E.A.; Berger, S.; Marks, J.; Brauman, J.I., Molecular Rotation and the Observation of Dipole-Bound States of Anions, J. Chem. Phys., 1993, 99, 10, 7586, https://doi.org/10.1063/1.465688 . [all data]

Zimmerman, Jackson, et al., 1978
Zimmerman, A.H.; Jackson, R.L.; Janousek, B.K.; Brauman, J.J., Electron photodetachment from cyclic enolate anions in the gas phase: Electron affinities of cyclic enolate radicals, J. Am. Chem. Soc., 1978, 100, 4674. [all data]

Brickhouse and Squires, 1988
Brickhouse, M.D.; Squires, R.R., Gas Phase Bronsted vs. Lewis Acid-Base Reactions of 6,6-Dimethylfulvene. A Sensitive Probe of the Electronic Structures of Organic Anions, J. Am. Chem. Soc., 1988, 110, 9, 2706, https://doi.org/10.1021/ja00217a002 . [all data]

Wickham-Jones, Ervin, et al., 1989
Wickham-Jones, C.T.; Ervin, K.M.; Ellison, G.B.; Lineberger, W.C., NH2 Electron Affinity, J. Chem. Phys., 1989, 91, 4, 2762, https://doi.org/10.1063/1.456994 . [all data]

MacKay, Hemsworth, et al., 1976
MacKay, G.J.; Hemsworth, R.S.; Bohme, D.K., Absolute gas-phase acidities of CH3NH2, C2H5NH2, (CH3)2NH, and (CH3)3N, Can. J. Chem., 1976, 54, 1624. [all data]

Check, Faust, et al., 2001
Check, C.E.; Faust, T.O.; Bailey, J.M.; Wright, B.J.; Gilbert, T.M.; Sunderlin, L.S., Addition of Polarization and Diffuse Functions to the LANL2DZ Basis Set for P-Block Elements, J. Phys. Chem. A,, 2001, 105, 34, 8111, https://doi.org/10.1021/jp011945l . [all data]

Meyer and Kass, 2010
Meyer, M.M.; Kass, S.R., Experimental and Theoretical Gas-Phase Acidities, Bond Dissociation Energies, and Heats of Formation of HClOx, x=1-4, J. Phys. Chem. A, 2010, 114, 12, 4086-4092, https://doi.org/10.1021/jp100888k . [all data]

Marcus, 1987
Marcus, Y., The Thermodynamics of Solvation of Ions. 2. The Enthalpy of Hydration at 298.15K, J. Chem. Soc. Farad. Trans. I, 1987, 83, 2, 339, https://doi.org/10.1039/f19878300339 . [all data]

Mallouk, Rosenthal, et al., 1984
Mallouk, T.E.; Rosenthal, G.L.; Muller, G.; Brusasco, R.; Bartlett, N., Fluoride ion affinities of GeF4 and BF4 from thermodynamic and structural data for (SF2)2GeF6, ClO2GeF5, and ClO2BF4, Inorg. Chem., 1984, 23, 3167. [all data]

Finch, Gates, et al., 1977
Finch, A.; Gates, P.N.; Peake, S.J., Thermochemistry of polyhalides. III. Cesium and rubidium tetrachloroiodates, J. Inorg. Nucl. Chem., 1977, 39, 2135. [all data]

Angel and Ervin, 2006
Angel, L.A.; Ervin, K.M., Gas-phase acidities and O-H bond dissociation enthalpies of phenol, 3-methylphenol, 2,4,6-trimethylphenol, and ethanoic acid, J. Phys. Chem. A, 2006, 110, 35, 10392-10403, https://doi.org/10.1021/jp0627426 . [all data]

Kebarle and McMahon, 1977
Kebarle, P.; McMahon, T.B., Intrinsic Acidities of Substituted Phenols and Benzoic Acids Determined by Gas Phase Proton Transfer Equilibria, J. Am. Chem. Soc., 1977, 99, 7, 2222, https://doi.org/10.1021/ja00449a032 . [all data]

Garand, Yacovitch, et al., 2010
Garand, E.; Yacovitch, T.I.; Zhou, J.; Sheehan, S.M.; Neumark, D.M., Slow photoelectron velocity-map imaging of the CnH- (n=5-9) anions, Chem. Sci., 2010, 1, 2, 192-201, https://doi.org/10.1039/c0sc00164c . [all data]

Natterer, Koch, et al., 1994
Natterer, J.; Koch, W.; Schroder, D.; Goldberg, N.; Schwarz, H., Combined experimental and theoretical study of the C-H bond strength and the gas phase acidity of triacetylene, C6H2, and the electron affinity of the C6H. radical, Chem. Phys. Lett., 1994, 229, 4-5, 429, https://doi.org/10.1016/0009-2614(94)01075-7 . [all data]

Chyall, Brickhouse, et al., 1994
Chyall, L.J.; Brickhouse, M.D.; Schnute, M.E.; Squires, R.R., Kinetic versus thermodynamic control in the deprotonation of unsymmetrical ketones in the gas phase, J. Am. Chem. Soc., 1994, 116, 19, 8681, https://doi.org/10.1021/ja00098a031 . [all data]

Zimmerman, Reed, et al., 1977
Zimmerman, A.H.; Reed, K.J.; Brauman, J.I., Photodetachment of electrons from enolate anions. Gas phase electron affinities of enolate radicals, J. Am. Chem. Soc., 1977, 99, 7203. [all data]

Engelking and Lineberger, 1977
Engelking, P.C.; Lineberger, W.C., Laser photoelectron spectrometry of C5H5-: A determination of the electron affinity and Jahn-Teller coupling in cyclopentadienyl, J. Chem. Phys., 1977, 67, 1412. [all data]

DePuy, Gronert, et al., 1989
DePuy, C.H.; Gronert, S.; Barlow, S.E.; Bierbaum, V.M.; Damrauer, R., The Gas Phase Acidities of the Alkanes, J. Am. Chem. Soc., 1989, 111, 6, 1968, https://doi.org/10.1021/ja00188a003 . [all data]

Seetula, Russell, et al., 1990
Seetula, J.A.; Russell, J.J.; Gutman, D., Kinetics and Thermochemistry of the Reactions of Alkyl Radicals with HI: A Reconciliation of the Alkyl Radical Heats of Formation, J. Am. Chem. Soc., 1990, 112, 4, 1347, https://doi.org/10.1021/ja00160a009 . [all data]

Peerboom, Rademaker, et al., 1992
Peerboom, R.A.L.; Rademaker, G.J.; Dekoning, L.J.; Nibbering, N.M.M., Stabilization of Cycloalkyl Carbanions in the Gas Phase, Rapid Commun. Mass Spectrom., 1992, 6, 6, 394, https://doi.org/10.1002/rcm.1290060608 . [all data]

Mihalick, Gatev, et al., 1996
Mihalick, J.E.; Gatev, G.G.; Brauman, J.I., Electron Photodetachment Spectroscopy of Solvated Anions: RO.HF- or ROH.F-?, J. Am. Chem. Soc., 1996, 118, 49, 12424, https://doi.org/10.1021/ja954202k . [all data]

Gal, Maria, et al., 1989
Gal, J.-F.; Maria, P.-C.; Decouzon, M., The Gas-Phase Acidity and Bond Dissociation Energies of Hydrogen Telluride, Int. J. Mass Spectrom. Ion Proc., 1989, 93, 1, 87, https://doi.org/10.1016/0168-1176(89)83076-9 . [all data]

Freidhoff, Snodgrass, et al., 1986
Freidhoff, C.B.; Snodgrass, J.T.; Coe, J.V.; McHugh, K.M.; Bowen, K.H., Negative ion photoelectron spectroscopy of TeH-, J. Chem. Phys., 1986, 84, 1051. [all data]

Meot-ner, Liebman, et al., 1988
Meot-ner, M.; Liebman, J.F.; Kafafi, S.A., Ionic Probes of Aromaticity in Annelated Rings, J. Am. Chem. Soc., 1988, 110, 18, 5937, https://doi.org/10.1021/ja00226a001 . [all data]

Kiefer, Zhang, et al., 1997
Kiefer, J.H.; Zhang, Q.; Kern, R.D.; Yao, J.; Jursic, B., Pyrolysis of Aromatic Azines: Pyrazine, Pyrimidine, and Pyridine, J. Phys. Chem. A, 1997, 101, 38, 7061, https://doi.org/10.1021/jp970211z . [all data]

Taft and Bordwell, 1988
Taft, R.W.; Bordwell, F.G., Structural and Solvent Effects Evaluated from Acidities Measured in Dimethyl Sulfoxide and in the Gas Phase, Acc. Chem. Res., 1988, 21, 12, 463, https://doi.org/10.1021/ar00156a005 . [all data]

Meot-ner and Kafafi, 1988
Meot-ner, M.; Kafafi, S.A., Carbon Acidities of Aromatic Compounds, J. Am. Chem. Soc., 1988, 110, 19, 6297, https://doi.org/10.1021/ja00227a003 . [all data]

Allison and McMahon, 1990
Allison, C.E.; McMahon, T.B., How Strong is the Si=C Bond in Fluoro- and Methyl Substituted Silaethylenes? An Experimental Determination of Pi Bond Strengths, J. Am. Chem. Soc., 1990, 112, 5, 1672, https://doi.org/10.1021/ja00161a002 . [all data]

Campanaro, Marvin, et al., 1988
Campanaro, A.; Marvin, C.H.; Morehouse, S.P.; McMahon, T.B., A Gas-phase Anionic Analog of the Wittig Reaction. An Ion Cyclotron Resonance Study of the Gas Phase Ion Chemistry of Silyl Carbanions., Org. Mass Spectrom., 1988, 23, 9, 663, https://doi.org/10.1002/oms.1210230907 . [all data]

Born, Ingemann, et al., 1994
Born, M.; Ingemann, S.; Nibbering, N.M.M., Heats of formation of mono-halogen-substituted carbenes. Stability and reactivity of CHX(center dot-) (X=F, Cl, Pr, and I) radical anions, J. Am. Chem. Soc., 1994, 116, 16, 7210, https://doi.org/10.1021/ja00095a025 . [all data]

Gilles, Ervin, et al., 1992
Gilles, M.K.; Ervin, K.M.; Ho, J.; Lineberger, W.C., Negative Ion Photoelectron Spectroscopy of HCF-, HCCl-, HCBr-, and HCI- - Photoelectron Angular Distributions and Neutral Triplet Excitation, J. Phys. Chem., 1992, 96, 3, 1130, https://doi.org/10.1021/j100182a021 . [all data]

Buker, Nibbering, et al., 1997
Buker, H.H.; Nibbering, N.M.M.; Espinosa, D.; Mongin, F.; Schlosser, M., Additivity of substituent effects in the fluoroarene series: Equilibrium acidity in the gas phase and deprotonation rates in ethereal solution, Tetrahed. Lett., 1997, 38, 49, 8519-8522, https://doi.org/10.1016/S0040-4039(97)10303-3 . [all data]

Briscese and Riveros, 1975
Briscese, S.M.J.; Riveros, J.M., Gas phase nucleophilic reactions of aromatic systems, J. Am. Chem. Soc., 1975, 97, 230. [all data]

Cheng and Grabowski, 1989
Cheng, X.; Grabowski, J.J., Gas-phase Acidity of Nitrobenzene from Flowing Afterglow Bracketing Studies, Rapid Commun. Mass Spectrom., 1989, 3, 2, 34-36, https://doi.org/10.1002/rcm.1290030207 . [all data]

Schmitt, Krempp, et al., 1992
Schmitt, R.J.; Krempp, M.; Bierbaum, V.M., Gas Phase Chemistry of Dinitramide and Nitroacetylide Ions, Int. J. Mass Spectrom. Ion Proc., 1992, 117, 621, https://doi.org/10.1016/0168-1176(92)80116-I . [all data]

Graul, Schnute, et al., 1990
Graul, S.T.; Schnute, M.E.; Squires, R.R., Gas-Phase Acidities of Carboxylic Acids and Alcohols from Collision-Induced Dissociation of Dimer Cluster Ions, Int. J. Mass Spectrom. Ion Proc., 1990, 96, 2, 181, https://doi.org/10.1016/0168-1176(90)87028-F . [all data]

Kuhn, Fenzlaff, et al., 1988
Kuhn, A.; Fenzlaff, H.-P.; Illenberger, E., Formation and Dissociation of Negative Ion Resonances in Methanol and Allyl Alcohol, J. Chem. Phys., 1988, 88, 12, 7453, https://doi.org/10.1063/1.454309 . [all data]

Bouby, Compton, et al., 1968
Bouby, L.; Compton, R.N.; Souleyrol, A., Formation d'ions negatifs dans l'alcool allylique et l'acroleine., Comptes Rendues. Acad. Sc. Paris, 1968, 266, 1250. [all data]

Majumdar, Clairet, et al., 1992
Majumdar, T.K.; Clairet, F.; Tabet, J.C.; Cooks, R.G., PAs of halogenated uridines, J. Am. Chem . Soc., 1992, 114, 2897. [all data]

Ramond, Blanksby, et al., 2002
Ramond, T.M.; Blanksby, S.J.; Kato, S.; Bierbaum, V.M.; Davico, G.E.; Schwartz, R.L.; Lineberger, W.C.; Elliso, Heat of formation of the hydroperoxyl radical HOO via negative ion studies, J. Phys. Chem. A, 2002, 106, 42, 9641-9647, https://doi.org/10.1021/jp014614h . [all data]

Bierbaum, Schmidt, et al., 1981
Bierbaum, V.M.; Schmidt, R.J.; DePuy, C.H.; Mead, R.H.; Schulz, P.A.; Lineberger, W.C., Reactions of carbanions with triplet and singlet molecular oxygen, J. Am. Chem. Soc., 1981, 103, 6262. [all data]

Leito, Raamat, et al., 2009
Leito, I.; Raamat, E.; Kutt, A.; Saame, J.; Kipper, K.; Koppel, I.A.; Koppel, I.; Zhang, M.; Mishima, M.; Yagupolskii, L.M.; Garlyauskayte, R.Y.; Filatov, A.A., Revision of the Gas-Phase Acidity Scale below 300 kcal mol(-1), J. Phys. Chem. A, 2009, 113, 29, 8421-8424, https://doi.org/10.1021/jp903780k . [all data]

Koppel, Koppel, et al., 1998
Koppel, I.; Koppel, J.; Maria, P.C.; Gal, J.F.; Notario, R.; Vlasov, V.M.; Taft, R.W., Comparison of Bronsted acidities of neutral NH-acids in gas phase, dimethyl sulfoxide and water, Int. J. Mass Spectrom., 1998, 175, 1-2, 61-69, https://doi.org/10.1016/S0168-1176(98)00113-X . [all data]

Dahlke and Kass, 1991
Dahlke, G.D.; Kass, S.R., Substituent Effects in the Gas Phase - 1-Substituted Allyl Anions, J. Am. Chem. Soc., 1991, 113, 15, 5566, https://doi.org/10.1021/ja00015a008 . [all data]

Poutsma, Nash, et al., 1997
Poutsma, J.C.; Nash, J.J.; Paulino, J.A.; Squires, R.R., Absolute Heats of Formation of Phenylcarbene and Vinylcarbene, J. Am. Chem. Soc., 1997, 119, 20, 4686, https://doi.org/10.1021/ja963918s . [all data]

Wenthold and Squires, 1995
Wenthold, P.G.; Squires, R.R., Determination of the gas-phase acidities of halogen-substituted aromatic compounds using the silane-cleavage method, J. Mass Spectrom., 1995, 30, 1, 17, https://doi.org/10.1002/jms.1190300105 . [all data]

Linnert and Riveros, 1994
Linnert, H.V.; Riveros, J.M., Benzyne-related mechanisms in the gas phase ion molecule reactions of haloarenes, Int. J. Mass Spectrom. Ion Proc., 1994, 140, 1, 163, https://doi.org/10.1016/0168-1176(94)04079-6 . [all data]

DePuy and Bierbaum, 1981
DePuy, C.H.; Bierbaum, V.M., Gas phase sulfur anions: Synthesis and reactions of H2NS- and related ions, Tetrahedron Lett., 1981, 22, 5129. [all data]

Bierbaum, Grabowski, et al., 1984
Bierbaum, V.M.; Grabowski, J.J.; DePuy, C.H., Gas-phase synthesis and reactions of nitrogen- and sulfur-containing anions, J. Phys. Chem., 1984, 88, 1389. [all data]

Clair and McMahon, 1980
Clair, R.L.; McMahon, T.B., An ion cyclotron resonance study of base-induced elimination reactions of fluorinated alcohols and unimolecular loss of HF from chemically activated fluoroalkoxide ions, Int. J. Mass Spectrom. Ion Phys., 1980, 33, 21. [all data]

Dawson and Jennings, 1977
Dawson, J.H.J.; Jennings, K.R., Relative gas phase acidities of some fluoroalcohols, Int. J. Mass Spectrom. Ion Phys., 1977, 25, 47. [all data]

Damrauer and Krempp, 1990
Damrauer, R.; Krempp, M., Gas Phase Ion-Molecule Chemistry of Methoxy-Substituted Silanes: Collision Induced Decomposition of Siloxide Ions Leading to Anions of Silaacetaldehyde and Methyl Silaformate, Organomet., 1990, 9, 4, 999, https://doi.org/10.1021/om00118a015 . [all data]

Froelicher, Freiser, et al., 1984
Froelicher, S.W.; Freiser, B.S.; Squires, R.R., Dimethylsilanone Enolate, J. Am. Chem. Soc., 1984, 106, 22, 6863, https://doi.org/10.1021/ja00334a077 . [all data]

Desai, Wu, et al., 1996
Desai, S.R.; Wu, H.; Wang, L.-S., Vibrationally Resolved Photoelectron Spectroscopy of AlO- and AlO2-, Int. J. Mass Spectrom. Ion Proc., 1996, 159, 1-3, 75, https://doi.org/10.1016/S0168-1176(96)04443-6 . [all data]

Damrauer, Krempp, et al., 1991
Damrauer, R.; Krempp, M.; Schmidt, M.W.; Gordon, M.S., Gas-Phase Chemistry of the Dimethylaluminum Oxide Ion and Related Aluminum Oxide Ions - Comparison of Reactivity with Siloxide Ions, J. Am. Chem. Soc., 1991, 113, 7, 2393, https://doi.org/10.1021/ja00007a007 . [all data]

Yang, Kiran, et al., 2004
Yang, X.; Kiran, B.; Wang, X.B.; Wang, L.S.; Mucha, M.; Jungwirth, P., Solvation of the azide anion (N-3(-)) in water clusters and aqueous interfaces: A combined investigation by photoelectron spectroscopy, density functional calculations, and molecular dynamic, J. Phys. Chem. A, 2004, 108, 39, 7820-7826, https://doi.org/10.1021/jp0496396 . [all data]

Pellerite, Jackson, et al., 1981
Pellerite, M.J.; Jackson, R.L.; Brauman, J.I., Proton affinity of the gaseous azide Ion. The N-H bond dissociation enegry in HN3, J. Phys. Chem., 1981, 85, 1624. [all data]

Franklin, Dibeler, et al., 1958
Franklin, J.L.; Dibeler, V.H.; Reese, R.M.; Krauss, M., Ionization and dissociation of hydrazoic acid and methyl azide by electron impact, J. Am. Chem. Soc., 1958, 80, 298. [all data]

Ingemann and Nibbering, 1985
Ingemann, S.; Nibbering, N.M.M., Gas phase chemistry of dipole stabilized carbanions derived from N,N-dimethylthioformamide and N,N-dimethylnitrosamine, Acta Chem. Scand., Ser. B, 1985, 39, 697. [all data]

Korsunskii, Pepekin, et al., 1967
Korsunskii, B.L.; Pepekin, V.I.; Lebedev, Yu.A.; Apin, A.Ya., Bull. Acad. Sci. USSR Div. Chem. Sci., 1967, 509. [all data]

Brinkman, Salomon, et al., 1995
Brinkman, E.A.; Salomon, K.; Tumas, W.; Brauman, J.I., Electron affinities and gas-phase acidities of organogermanium and organotin compounds, J. Am. Chem. Soc., 1995, 117, 17, 4905, https://doi.org/10.1021/ja00122a022 . [all data]

Wenthold, Hu, et al., 1999
Wenthold, P.G.; Hu, J.; Squires, R.R.; Lineberger, W.C., Photoelectron spectroscopy of the trimethylenemethane negative ion, J. Am. Soc. Mass Spectrom., 1999, 10, 9, 800-809, https://doi.org/10.1016/S1044-0305(99)00043-4 . [all data]

Wenthold, Polak, et al., 1996
Wenthold, P.G.; Polak, M.L.; Lineberger, W.C., Photoelectron Spectroscopy of the Allyl and 2-Methylallyl Anions, J. Phys. Chem., 1996, 100, 17, 6920, https://doi.org/10.1021/jp953401n . [all data]

Bartmess and Burnham, 1984
Bartmess, J.E.; Burnham, R., Effect of central substituents on the gas phase acidities of propenes, J. Org. Chem., 1984, 49, 1382. [all data]

Kass and DePuy, 1985
Kass, S.R.; DePuy, C.H., Gas phase ion chemistry of azides. The generation of CH=N- and CH2=NCH2-, J. Org. Chem., 1985, 50, 2874. [all data]

Jones, Bernier, et al., 2007
Jones, C.M.; Bernier, M.; Carson, E.; Colyer, K.E.; Metz, R.; Pawlow, A.; Wischow, E.D.; Webb, I.; Andriole, E.J.; Poutsma, J.C., Gas-phase Acities of the 20 Protein Amino Acids, Int. J. Mass Spectrom., 2007, 267, 1-3, 54-62, https://doi.org/10.1016/j.ijms.2007.02.018 . [all data]

Caldwell, Renneboog, et al., 1989
Caldwell, G.; Renneboog, R.; Kebarle, P., Gas Phase Acidities of Aliphatic Carboxylic Acids, Based on Measurements of Proton Transfer Equilibria, Can. J. Chem., 1989, 67, 4, 661, https://doi.org/10.1139/v89-092 . [all data]

Locke and McIver, 1983
Locke, M.J.; McIver, R.T., Jr., Effect of Solvation on the Acid/Base Properties of Glycine, J. Am. Chem. Soc., 1983, 105, 4226. [all data]

Muftakhov, Vasil'ev, et al., 1999
Muftakhov, M.V.; Vasil'ev, Y.V.; Mazunov, V.A., Determination of electron affinity of carbonyl radicals by means of negative ion mass spectrometry, Rapid Commun. Mass Spectrom., 1999, 13, 12, 1104-1108, https://doi.org/10.1002/(SICI)1097-0231(19990630)13:12<1104::AID-RCM619>3.0.CO;2-C . [all data]

Grabowski and Owusu
Grabowski, J.J.; Owusu, D., , as cited in 98CLI/WEN. [all data]

DePuy, Kass, et al., 1988
DePuy, C.H.; Kass, S.R.; Bean, G.P., Formation and Reactions of Heteroaromatic Anions in the Gas Phase, J. Org. Chem., 1988, 53, 19, 4427, https://doi.org/10.1021/jo00254a001 . [all data]

Smith, Kim, et al., 1997
Smith, J.R.; Kim, J.B.; Lineberger, W.C., High-resolution Threshold Photodetachment Spectroscopy of OH-, Phys. Rev. A, 1997, 55, 3, 2036, https://doi.org/10.1103/PhysRevA.55.2036 . [all data]

Matimba, Crabbendam, et al., 1992
Matimba, H.E.K.; Crabbendam, A.M.; Ingemann, S.; Nibbering, N.M.M., Gas-phase Bimolecular Chemistry of the .-CHNC and .-CHCN Radical Anions, Int. J. Mass Spectrom. Ion Proc., 1992, 114, 1-2, 85, https://doi.org/10.1016/0168-1176(92)85024-T . [all data]

Filley, DePuy, et al., 1987
Filley, J.; DePuy, C.H.; Bierbaum, V.M., Gas-Phase Negative Ion Chemistry of Methyl Isocyanide, J. Am. Chem. Soc., 1987, 109, 20, 5992, https://doi.org/10.1021/ja00254a017 . [all data]

Blondel, Chaibi, et al., 2005
Blondel, C.; Chaibi, W.; Delsart, C.; Drag, C.; Goldfarb, F.; Kroger, S., The electron affinities of O, Si, and S revisited with the photodetachment microscope, Eur. Phys. J. D, 2005, 33, 3, 335-342, https://doi.org/10.1140/epjd/e2005-00069-9 . [all data]

Blondel, Delsart, et al., 2001
Blondel, C.; Delsart, C.; Goldfarb, F., Electron spectrometry at the mu eV level and the electron affinities of Si and F, J. Phys. B: Atom. Mol. Opt. Phys., 2001, 34, 9, L281-L288, https://doi.org/10.1088/0953-4075/34/9/101 . [all data]

Rempala and Ervin, 2000
Rempala, K.; Ervin, K.M., Collisional activation of the Endoergic Hydrogen Atom Transfer Reaction S-(2P) + H2 - SH- + H, J. Chem. Phys., 2000, 112, 10, 4579, https://doi.org/10.1063/1.481016 . [all data]

Gianola, Ichino, et al., 2005
Gianola, A.J.; Ichino, T.; Hoenigman, R.L.; Kato, S.; Bierbaum, V.M.; Lineberger, W.C., Photoelectron spectra and ion chemistry of imidazolide, J. Phys. Chem. A, 2005, 109, 50, 11504-11514, https://doi.org/10.1021/jp053566o . [all data]

Taft, Anvia, et al., 1986
Taft, R.W.; Anvia, F.; Taagepera, M.; Catalan, J.; Elgueroy, J., Electrostatic proximity effects in the relative basicities of pyrazole, imidazole, pyridazine, and pyrimidine, J. Am. Chem. Soc., 1986, 108, 3237. [all data]

Koppel, Taft, et al., 1994
Koppel, I.A.; Taft, R.W.; Anvia, F.; Zhu, S.Z.; Hu, L.Q.; Sung, K.S.; Desmarteau, D.D.; Yagupolskii, L.M., The Gas-Phase Acidities of Very Strong Neutral Bronsted Acids, J. Am. Chem. Soc., 1994, 116, 7, 3047, https://doi.org/10.1021/ja00086a038 . [all data]


Notes

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