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 201 to 250

C7H6NO2- + Hydrogen cation = Benzene, 1-methyl-4-nitro-

By formula: C7H6NO2- + H+ = C7H7NO2

Quantity Value Units Method Reference Comment
Δr1475. ± 8.8kJ/molG+TSTaft and Topsom, 1987gas phase; value altered from reference due to change in acidity scale
Δr1477. ± 10.kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Δr1445. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase; value altered from reference due to change in acidity scale
Δr1447. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C19H15- + Hydrogen cation = Triphenylmethane

By formula: C19H15- + H+ = C19H16

Quantity Value Units Method Reference Comment
Δr1501. ± 9.2kJ/molG+TSTaft and Bordwell, 1988gas phase
Δr1510. ± 10.kJ/molG+TSBartmessgas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr1467. ± 8.4kJ/molIMRETaft and Bordwell, 1988gas phase
Δr1476. ± 9.6kJ/molIMREBartmessgas phase; value altered from reference due to change in acidity scale

C2H6N- + Hydrogen cation = Dimethylamine

By formula: C2H6N- + H+ = C2H7N

Quantity Value Units Method Reference Comment
Δr1653. ± 8.4kJ/molD-EARadisic, Xu, et al., 2002gas phase; BDE supported by 72GOL/SOL, over McMillen and Golden, 1982
Δr1658.7 ± 3.7kJ/molG+TSMacKay, Hemsworth, et al., 1976gas phase
Quantity Value Units Method Reference Comment
Δr1623. ± 8.8kJ/molH-TSRadisic, Xu, et al., 2002gas phase; BDE supported by 72GOL/SOL, over McMillen and Golden, 1982
Δr1628.4 ± 2.5kJ/molIMREMacKay, Hemsworth, et al., 1976gas phase

CNS- + Hydrogen cation = Isothiocyanic acid

By formula: CNS- + H+ = CHNS

Quantity Value Units Method Reference Comment
Δr<1361. ± 4.6kJ/molD-EABradforth, Kim, et al., 1993gas phase; Acid HNCS. HSCN up by ca. 8 kcal/mol
Δr1375. ± 21.kJ/molG+TSBierbaum, Grabowski, et al., 1984gas phase; Acid: HNCS
Quantity Value Units Method Reference Comment
Δr<1329. ± 5.9kJ/molH-TSBradforth, Kim, et al., 1993gas phase; Acid HNCS. HSCN up by ca. 8 kcal/mol
Δr1343. ± 21.kJ/molIMRBBierbaum, Grabowski, et al., 1984gas phase; Acid: HNCS

C10H7- + Hydrogen cation = Azulene

By formula: C10H7- + H+ = C10H8

Quantity Value Units Method Reference Comment
Δr1538. ± 10.kJ/molTDEqMeot-ner, Liebman, et al., 1988gas phase; Acidity seriously disagrees with high level calculations. Dissociative to acetylide? C-3is most acidic site by G3MP2B3 calns.
Quantity Value Units Method Reference Comment
Δr1507. ± 8.4kJ/molTDEqMeot-ner, Liebman, et al., 1988gas phase; Acidity seriously disagrees with high level calculations. Dissociative to acetylide? C-3is most acidic site by G3MP2B3 calns.

C3H2F3O- + Hydrogen cation = 2-Propanone, 1,1,1-trifluoro-

By formula: C3H2F3O- + H+ = C3H3F3O

Quantity Value Units Method Reference Comment
Δr1461. ± 8.8kJ/molG+TSTaft, 1987gas phase; value altered from reference due to change in acidity scale
Δr1466. ± 15.kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Δr1431. ± 8.4kJ/molIMRETaft, 1987gas phase; value altered from reference due to change in acidity scale
Δr1436. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C6H2N3O7- + Hydrogen cation = Picric acid

By formula: C6H2N3O7- + H+ = C6H3N3O7

Quantity Value Units Method Reference Comment
Δr1298. ± 9.2kJ/molG+TSKoppel, Taft, et al., 1994gas phase; Per Leito, Raamat, et al., 2009, dGacid is likely too weak by up to 1.3 kcal/mol.
Quantity Value Units Method Reference Comment
Δr1267. ± 8.4kJ/molIMREKoppel, Taft, et al., 1994gas phase; Per Leito, Raamat, et al., 2009, dGacid is likely too weak by up to 1.3 kcal/mol.
Δr<1292.9kJ/molIMRBDzidic, Carroll, et al., 1974gas phase; I- deprotonates

C8H6NO4- + Hydrogen cation = C8H7NO4

By formula: C8H6NO4- + H+ = C8H7NO4

Quantity Value Units Method Reference Comment
Δr1317. ± 13.kJ/molD-EAWang, Broadus, et al., 2000gas phase; Vertical Detachment Energy: 5.02±0.05 eV
Δr1304. ± 21.kJ/molG+TSBroadus and Kass, 2000gas phase
Quantity Value Units Method Reference Comment
Δr1286. ± 14.kJ/molH-TSWang, Broadus, et al., 2000gas phase; Vertical Detachment Energy: 5.02±0.05 eV
Δr1273. ± 21.kJ/molIMRBBroadus and Kass, 2000gas phase

CNO- + Hydrogen cation = Isocyanic acid

By formula: CNO- + H+ = CHNO

Quantity Value Units Method Reference Comment
Δr1427.5 ± 2.6kJ/molD-EABradforth, Kim, et al., 1993gas phase; D-EA cycle requires a DH ca 4 kcal/mol weaker
Δr1442. ± 8.8kJ/molG+TSWight and Beauchamp, 1980gas phase
Quantity Value Units Method Reference Comment
Δr1400.6 ± 3.0kJ/molH-TSBradforth, Kim, et al., 1993gas phase; D-EA cycle requires a DH ca 4 kcal/mol weaker
Δr1415. ± 8.4kJ/molIMREWight and Beauchamp, 1980gas phase

CClF2- + Hydrogen cation = Difluorochloromethane

By formula: CClF2- + H+ = CHClF2

Quantity Value Units Method Reference Comment
Δr>1567.8kJ/molAcidPaulino and Squires, 1991gas phase; Probably CF2..Cl-, non-covalent.
Δr1583. ± 29.kJ/molD-EADispert and Lacmann, 1978gas phase; From CF2Cl2
Quantity Value Units Method Reference Comment
Δr>1535.4 ± 3.7kJ/molH-TSPaulino and Squires, 1991gas phase; Probably CF2..Cl-, non-covalent.
Δr1550. ± 30.kJ/molH-TSDispert and Lacmann, 1978gas phase; From CF2Cl2

C4H5- + Hydrogen cation = 2-Butyne

By formula: C4H5- + H+ = C4H6

Quantity Value Units Method Reference Comment
Δr1628. ± 8.8kJ/molG+TSGal, Decouzon, et al., 2001gas phase; Acid: MeC≡CMe
Δr1628. ± 14.kJ/molG+TSN/Agas phase; Measured vs pyridine
Quantity Value Units Method Reference Comment
Δr1597. ± 8.4kJ/molIMREGal, Decouzon, et al., 2001gas phase; Acid: MeC≡CMe
Δr1596. ± 13.kJ/molIMREN/Agas phase; Measured vs pyridine

thiophenoxide anion + Hydrogen cation = Benzenethiol

By formula: C6H5S- + H+ = C6H6S

Quantity Value Units Method Reference Comment
Δr1424. ± 8.8kJ/molG+TSTaft and Bordwell, 1988gas phase
Δr>1423. ± 7.5kJ/molD-EARichardson, Stephenson, et al., 1975gas phase
Quantity Value Units Method Reference Comment
Δr1395. ± 8.8kJ/molIMREGuillemin, Riague, et al., 2005gas phase
Δr1397. ± 8.4kJ/molIMRETaft and Bordwell, 1988gas phase
Δr>1395. ± 7.9kJ/molH-TSRichardson, Stephenson, et al., 1975gas phase

C4H4NO2- + Hydrogen cation = Acetic acid, cyano-, methyl ester

By formula: C4H4NO2- + H+ = C4H5NO2

Quantity Value Units Method Reference Comment
Δr1426. ± 8.8kJ/molG+TSMishima, Matsuoka, et al., 2004gas phase; Calc: keto form of acid more stable.
Δr1425. ± 8.8kJ/molG+TSTaft, Abboud, et al., 1988gas phase
Quantity Value Units Method Reference Comment
Δr1400. ± 8.4kJ/molIMREMishima, Matsuoka, et al., 2004gas phase; Calc: keto form of acid more stable.
Δr1399. ± 8.4kJ/molIMRETaft, Abboud, et al., 1988gas phase

C2F3O- + Hydrogen cation = C2HF3O

By formula: C2F3O- + H+ = C2HF3O

Quantity Value Units Method Reference Comment
Δr>1623. ± 17.kJ/molD-EAHarland and Thynne, 1970gas phase; From (CF3)2CO. Values unreasonable: ΔHf(CF3CO-)must be less than ΔHf(CF3-+CO)=-181. G3MP2B3 EA = 1.6 eV
Quantity Value Units Method Reference Comment
Δr>1590. ± 17.kJ/molH-TSHarland and Thynne, 1970gas phase; From (CF3)2CO. Values unreasonable: ΔHf(CF3CO-)must be less than ΔHf(CF3-+CO)=-181. G3MP2B3 EA = 1.6 eV

C9H7- + Hydrogen cation = Benzene, 1-ethynyl-4-methyl-

By formula: C9H7- + H+ = C9H8

Quantity Value Units Method Reference Comment
Δr1555. ± 9.6kJ/molG+TSChabinyc and Brauman, 1999gas phase; reported as 365.2/372.8, relative to MeOH at 375.2; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr1523. ± 8.4kJ/molIMREChabinyc and Brauman, 1999gas phase; reported as 365.2/372.8, relative to MeOH at 375.2; value altered from reference due to change in acidity scale

CCl2F- + Hydrogen cation = Fluorodichloromethane

By formula: CCl2F- + H+ = CHCl2F

Quantity Value Units Method Reference Comment
Δr1503.6kJ/molAcidPoutsma, Paulino, et al., 1997gas phase
Δr1507. ± 8.8kJ/molG+TSPoutsma, Paulino, et al., 1997gas phase
Δr<1506. ± 20.kJ/molD-EAIllenberger, Baumgartel, et al., 1979gas phase; From CF2Cl2
Quantity Value Units Method Reference Comment
Δr1471.2 ± 2.5kJ/molH-TSPoutsma, Paulino, et al., 1997gas phase
Δr1475. ± 8.4kJ/molIMRBPoutsma, Paulino, et al., 1997gas phase

C15H11- + Hydrogen cation = Anthracene, 9-methyl-

By formula: C15H11- + H+ = C15H12

Quantity Value Units Method Reference Comment
Δr1515. ± 10.kJ/molG+TSBartmess and Griffiths, 1990gas phase; Isomer 9-methylene-9,10-dihydroanthracene: ΔG=349.0±3.0, ΔS=27.0, ΔH=357.1;DH: Zhang, Bordwell, et al., 1993
Quantity Value Units Method Reference Comment
Δr1486. ± 9.6kJ/molIMREBartmess and Griffiths, 1990gas phase; Isomer 9-methylene-9,10-dihydroanthracene: ΔG=349.0±3.0, ΔS=27.0, ΔH=357.1;DH: Zhang, Bordwell, et al., 1993

C8H7O2- + Hydrogen cation = Benzoic acid, 4-methyl-

By formula: C8H7O2- + H+ = C8H8O2

Quantity Value Units Method Reference Comment
Δr1427. ± 8.8kJ/molG+TSKebarle and McMahon, 1977gas phase
Δr1425. ± 8.8kJ/molG+TSDecouzon, Exner, et al., 1996gas phase; relative to benzoate at 333.0 kcal/mol
Quantity Value Units Method Reference Comment
Δr1397. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase
Δr1396. ± 8.4kJ/molIMREDecouzon, Exner, et al., 1996gas phase; relative to benzoate at 333.0 kcal/mol

C8H7O2- + Hydrogen cation = Benzoic acid, 3-methyl-

By formula: C8H7O2- + H+ = C8H8O2

Quantity Value Units Method Reference Comment
Δr1425. ± 8.8kJ/molG+TSKebarle and McMahon, 1977gas phase
Δr1424. ± 8.8kJ/molG+TSDecouzon, Exner, et al., 1996gas phase; Relative to benzoate at 333.0 kcal/mol
Quantity Value Units Method Reference Comment
Δr1396. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase
Δr1395. ± 8.4kJ/molIMREDecouzon, Exner, et al., 1996gas phase; Relative to benzoate at 333.0 kcal/mol

HBe- + Hydrogen cation = Beryllium hydride

By formula: HBe- + H+ = H2Be

Quantity Value Units Method Reference Comment
Δr1630. ± 13.kJ/molD-EARackwitz, Feldman, et al., 1977gas phase; ΔHf(BeH2){ Chase Jr., Davies, et al., 1985} is 1959 SWAG. G3(MP2)calcn(JEB): ΔHf=44.5kcal, BDE=92.1, ΔHacid=389.7
Quantity Value Units Method Reference Comment
Δr1595. ± 13.kJ/molH-TSRackwitz, Feldman, et al., 1977gas phase; ΔHf(BeH2){ Chase Jr., Davies, et al., 1985} is 1959 SWAG. G3(MP2)calcn(JEB): ΔHf=44.5kcal, BDE=92.1, ΔHacid=389.7

CHF2- + Hydrogen cation = Difluoromethane

By formula: CHF2- + H+ = CH2F2

Quantity Value Units Method Reference Comment
Δr1628. ± 15.kJ/molCIDTGraul and Squires, 1990gas phase; G2 calculations( Lee, Dyke, et al., 1998) predict ΔHacid = 399 kcal/mol
Quantity Value Units Method Reference Comment
Δr1595. ± 15.kJ/molH-TSGraul and Squires, 1990gas phase; G2 calculations( Lee, Dyke, et al., 1998) predict ΔHacid = 399 kcal/mol
Δr1586. ± 25.kJ/molIMRBSullivan, 1977gas phase

Carbon anion + Hydrogen cation = C2H

By formula: C2- + H+ = C2H

Quantity Value Units Method Reference Comment
Δr>1460. ± 15.kJ/molD-EAArnold, Bradforth, et al., 1991gas phase
Δr<1572. ± 9.6kJ/molG+TSSchiff and Bohme, 1975gas phase; No reaction with acetylene
Quantity Value Units Method Reference Comment
Δr>1430. ± 16.kJ/molH-TSArnold, Bradforth, et al., 1991gas phase
Δr<1542. ± 8.4kJ/molIMRBSchiff and Bohme, 1975gas phase; No reaction with acetylene

C4H5O- + Hydrogen cation = Methacrolein

By formula: C4H5O- + H+ = C4H6O

Quantity Value Units Method Reference Comment
Δr1576. ± 13.kJ/molG+TSKleingeld and Nibbering, 1984gas phase; Acid: 2-methylpropenal. Reprotonation to dimethyl ketene? G3MP2B3 calculations indicate a dHacid of 396 kcal/mol
Quantity Value Units Method Reference Comment
Δr1544. ± 13.kJ/molIMRBKleingeld and Nibbering, 1984gas phase; Acid: 2-methylpropenal. Reprotonation to dimethyl ketene? G3MP2B3 calculations indicate a dHacid of 396 kcal/mol

C4H7O2- + Hydrogen cation = Butanoic acid

By formula: C4H7O2- + H+ = C4H8O2

Quantity Value Units Method Reference Comment
Δr1451. ± 8.4kJ/molTDEqNorrman and McMahon, 1999gas phase
Δr1450. ± 9.2kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Δr1450. ± 9.2kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Δr1420. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase
Δr1420. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C3H7- + Hydrogen cation = Propane

By formula: C3H7- + H+ = C3H8

Quantity Value Units Method Reference Comment
Δr1755. ± 8.4kJ/molBranDePuy, Gronert, et al., 1989gas phase
Δr1755. ± 20.kJ/molBranPeerboom, Rademaker, et al., 1992gas phase
Δr1753. ± 8.4kJ/molBranDePuy, Bierbaum, et al., 1984gas phase
Quantity Value Units Method Reference Comment
Δr1721. ± 8.8kJ/molH-TSDePuy, Gronert, et al., 1989gas phase
Δr1722. ± 21.kJ/molH-TSPeerboom, Rademaker, et al., 1992gas phase

CH3S2- + Hydrogen cation = Methyl hydrogen disulfide

By formula: CH3S2- + H+ = CH4S2

Quantity Value Units Method Reference Comment
Δr1471. ± 13.kJ/molG+TSDownard, Bowie, et al., 1992gas phase; Acid: between CF3COCH3, tBuSH
Δr1471. ± 17.kJ/molD-EAMoran and Ellison, 1988gas phase
Quantity Value Units Method Reference Comment
Δr1443. ± 13.kJ/molIMRBDownard, Bowie, et al., 1992gas phase; Acid: between CF3COCH3, tBuSH
Δr1443. ± 17.kJ/molH-TSMoran and Ellison, 1988gas phase

C7H6NO2 + Hydrogen cation = Trigonelline

By formula: C7H6NO2 + H+ = C7H7NO2

Quantity Value Units Method Reference Comment
Δr1507. ± 21.kJ/molD-EAWang, Broadus, et al., 2000gas phase; ArCO2-: EAad = 3.8±0.1 eV
Δr1448. ± 21.kJ/molG+TSBroadus and Kass, 2000gas phase
Quantity Value Units Method Reference Comment
Δr1474. ± 21.kJ/molH-TSWang, Broadus, et al., 2000gas phase; ArCO2-: EAad = 3.8±0.1 eV
Δr1415. ± 21.kJ/molIMRBBroadus and Kass, 2000gas phase

C5H9O- + Hydrogen cation = Cyclopentanol

By formula: C5H9O- + H+ = C5H10O

Quantity Value Units Method Reference Comment
Δr1602. ± 19.kJ/molD-EAAlconcel and Continetti, 2002gas phase; derived acidity seems ca. 10 kcal/mol too weak, and EA likewise
Quantity Value Units Method Reference Comment
Δr1535. ± 4.6kJ/molN/AGarver, Yang, et al., 2011gas phase
Δr1569. ± 20.kJ/molH-TSAlconcel and Continetti, 2002gas phase; derived acidity seems ca. 10 kcal/mol too weak, and EA likewise

C4H3N2- + Hydrogen cation = 1,3-Diazine

By formula: C4H3N2- + H+ = C4H4N2

Quantity Value Units Method Reference Comment
Δr1612. ± 10.kJ/molTDEqMeot-ner and Kafafi, 1988gas phase; Acid: pyrimidine. Anchored to 88MEO scale, not "87 acidity scale
Quantity Value Units Method Reference Comment
Δr1576.5 ± 2.9kJ/molN/AWren, Vogelhuber, et al., 2012gas phase
Δr1577. ± 8.4kJ/molTDEqMeot-ner and Kafafi, 1988gas phase; Acid: pyrimidine. Anchored to 88MEO scale, not "87 acidity scale

C4H3N2- + Hydrogen cation = Pyridazine

By formula: C4H3N2- + H+ = C4H4N2

Quantity Value Units Method Reference Comment
Δr1600. ± 10.kJ/molTDEqMeot-ner and Kafafi, 1988gas phase; Pyridazine. Anchored to 88MEO scale, not the "87 Acidity Scale".
Quantity Value Units Method Reference Comment
Δr1564.8 ± 2.9kJ/molN/AWren, Vogelhuber, et al., 2012gas phase
Δr1562. ± 8.4kJ/molTDEqMeot-ner and Kafafi, 1988gas phase; Pyridazine. Anchored to 88MEO scale, not the "87 Acidity Scale".

C2H7Si- + Hydrogen cation = Silane, dimethyl-

By formula: C2H7Si- + H+ = C2H8Si

Quantity Value Units Method Reference Comment
Δr1594. ± 8.8kJ/molD-EABrinkman, Berger, et al., 1994gas phase
Δr1610. ± 17.kJ/molG+TSDamrauer, Kass, et al., 1988gas phase; Between furan and methanol.
Quantity Value Units Method Reference Comment
Δr1561. ± 9.2kJ/molH-TSBrinkman, Berger, et al., 1994gas phase
Δr1577. ± 17.kJ/molIMRBDamrauer, Kass, et al., 1988gas phase; Between furan and methanol.

C6H4NO2- + Hydrogen cation = Niacin

By formula: C6H4NO2- + H+ = C6H5NO2

Quantity Value Units Method Reference Comment
Δr1399. ± 8.4kJ/molCIDCSchafman and Wenthold, 2007gas phase
Δr1395. ± 12.kJ/molG+TSBreuker, Knochenmuss, et al., 1999gas phase; Acid: nicotinic acid
Quantity Value Units Method Reference Comment
Δr1370. ± 9.2kJ/molH-TSSchafman and Wenthold, 2007gas phase
Δr1366. ± 11.kJ/molIMRBBreuker, Knochenmuss, et al., 1999gas phase; Acid: nicotinic acid

C6H15OSi- + Hydrogen cation = Triethylsilanol

By formula: C6H15OSi- + H+ = C6H16OSi

Quantity Value Units Method Reference Comment
Δr1497. ± 9.2kJ/molG+TSGrimm and Bartmess, 1992gas phase
Δr1504. ± 17.kJ/molG+TSDamrauer, Simon, et al., 1991gas phase; between pyrrole, CF3CH2OH
Quantity Value Units Method Reference Comment
Δr1471. ± 8.4kJ/molIMREGrimm and Bartmess, 1992gas phase
Δr1477. ± 17.kJ/molIMRBDamrauer, Simon, et al., 1991gas phase; between pyrrole, CF3CH2OH

C2H6O3P- + Hydrogen cation = Dimethyl phosphite

By formula: C2H6O3P- + H+ = C2H7O3P

Quantity Value Units Method Reference Comment
Δr1492. ± 15.kJ/molG+TSMcDonald, Chowdhury, et al., 1987gas phase; Acidity between MeNO2, EtSH. Acid taken as (MeO)2P(O)H.
Quantity Value Units Method Reference Comment
Δr1461. ± 15.kJ/molIMRBMcDonald, Chowdhury, et al., 1987gas phase; Acidity between MeNO2, EtSH. Acid taken as (MeO)2P(O)H.
Δr1469. ± 17.kJ/molIMRBAnderson, DePuy, et al., 1984gas phase; Between MeSH, H2S

C2H3O2- + Hydrogen cation = Methyl formate

By formula: C2H3O2- + H+ = C2H4O2

Quantity Value Units Method Reference Comment
Δr<1606.7kJ/molCIDTGraul and Squires, 1988gas phase
Δr<1639.1 ± 3.8kJ/molG+TSDePuy, Grabowski, et al., 1985gas phase; HO- + DCO2CH3 -> (M-D)-. ΔHf(MeO- + CO) = -59.7 kcal/mol
Quantity Value Units Method Reference Comment
Δr<1606.7kJ/molIMRBDePuy, Grabowski, et al., 1985gas phase; HO- + DCO2CH3 -> (M-D)-. ΔHf(MeO- + CO) = -59.7 kcal/mol

CHN2- + Hydrogen cation = 3H-Diazirine

By formula: CHN2- + H+ = CH2N2

Quantity Value Units Method Reference Comment
Δr1681. ± 13.kJ/molG+TSKroeker and Kass, 1990gas phase; Between MeNH2, EtNH2. The expt dHf(diazirine) disagrees with numerous l calculations by -14 kcal/mol
Quantity Value Units Method Reference Comment
Δr1648. ± 13.kJ/molIMRBKroeker and Kass, 1990gas phase; Between MeNH2, EtNH2. The expt dHf(diazirine) disagrees with numerous l calculations by -14 kcal/mol

BF2- + Hydrogen cation = Difluoroborane

By formula: BF2- + H+ = HBF2

Quantity Value Units Method Reference Comment
Δr1564. ± 26.kJ/molD-EASrivastava, Uy, et al., 1974gas phase; EA: 29.2 kcal < EA(F), new EA(F) used. Too stable by ca. 24 kcal/mol, relative to G3(MP2)B3 calcs.
Quantity Value Units Method Reference Comment
Δr1533. ± 26.kJ/molH-TSSrivastava, Uy, et al., 1974gas phase; EA: 29.2 kcal < EA(F), new EA(F) used. Too stable by ca. 24 kcal/mol, relative to G3(MP2)B3 calcs.

C2H5Si- + Hydrogen cation = (CH3)2Si

By formula: C2H5Si- + H+ = C2H6Si

Quantity Value Units Method Reference Comment
Δr1593. ± 21.kJ/molG+TSDamrauer, DePuy, et al., 1986gas phase; May have rearranged to 2-sila-allyl anion: G3MP2B3 calculations indicate an acidity of 361 kcal/mol
Quantity Value Units Method Reference Comment
Δr1565. ± 21.kJ/molIMRBDamrauer, DePuy, et al., 1986gas phase; May have rearranged to 2-sila-allyl anion: G3MP2B3 calculations indicate an acidity of 361 kcal/mol

C2H4NO- + Hydrogen cation = Acetamide

By formula: C2H4NO- + H+ = C2H5NO

Quantity Value Units Method Reference Comment
Δr1515. ± 8.8kJ/molG+TSDecouzon, Exner, et al., 1990gas phase; value altered from reference due to change in acidity scale
Δr1500. ± 5.0kJ/molEIAEMuftakhov, Vasil'ev, et al., 1999gas phase
Quantity Value Units Method Reference Comment
Δr1485. ± 8.4kJ/molIMREDecouzon, Exner, et al., 1990gas phase; value altered from reference due to change in acidity scale

C3F5O- + Hydrogen cation = 2-Propanone, 1,1,1,3,3-pentafluoro-

By formula: C3F5O- + H+ = C3HF5O

Quantity Value Units Method Reference Comment
Δr1412. ± 18.kJ/molG+TSFarid and McMahon, 1980gas phase; Between FCH2CO2H, HCl; nearer to HCl; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Δr1384. ± 17.kJ/molIMRBFarid and McMahon, 1980gas phase; Between FCH2CO2H, HCl; nearer to HCl; value altered from reference due to change in acidity scale

CF3S- + Hydrogen cation = Methanethiol, trifluoro-

By formula: CF3S- + H+ = CHF3S

Quantity Value Units Method Reference Comment
Δr1400. ± 9.6kJ/molG+TSKoppel, Pihl, et al., 1994gas phase; Possibly dissociative protonation -> CF2S + HF + A-. See CF3O-. G2: 321.0, Burk, Koppel, et al., 2000
Quantity Value Units Method Reference Comment
Δr1370. ± 8.4kJ/molIMREKoppel, Pihl, et al., 1994gas phase; Possibly dissociative protonation -> CF2S + HF + A-. See CF3O-. G2: 321.0, Burk, Koppel, et al., 2000

CH3S- + Hydrogen cation = Methanethiol

By formula: CH3S- + H+ = CH4S

Quantity Value Units Method Reference Comment
Δr1654. ± 11.kJ/molG+TSKass, Guo, et al., 1990gas phase; Acidity between D2O and Me2NH.
Δr1638. ± 32.kJ/molD-EAKass, Guo, et al., 1990gas phase; Between O2 and SO2. Explains bad anchor in McIver Jr. and Fukuda, 1982
Quantity Value Units Method Reference Comment
Δr1624. ± 10.kJ/molIMRBKass, Guo, et al., 1990gas phase; Acidity between D2O and Me2NH.

H3Sn- + Hydrogen cation = H4Sn

By formula: H3Sn- + H+ = H4Sn

Quantity Value Units Method Reference Comment
Δr1466. ± 8.8kJ/molG+TSGal, Decouzon, et al., 2001gas phase
Δr1461.9kJ/molN/ACheck, Faust, et al., 2001gas phase; NiH2; ; ΔS(EA)=10.0
Quantity Value Units Method Reference Comment
Δr1432. ± 8.4kJ/molIMREGal, Decouzon, et al., 2001gas phase
Δr1428.4kJ/molN/ACheck, Faust, et al., 2001gas phase; NiH2; ; ΔS(EA)=10.0

C8H5O- + Hydrogen cation = Benzocyclobuten-1(2H)-one

By formula: C8H5O- + H+ = C8H6O

Quantity Value Units Method Reference Comment
Δr1505. ± 9.2kJ/molG+TSBroadus and Kass, 1999gas phase; Correction to direction of ΔGacid reported in literature: Kass, private communication
Quantity Value Units Method Reference Comment
Δr1473. ± 8.8kJ/molIMREBroadus and Kass, 1999gas phase; Correction to direction of ΔGacid reported in literature: Kass, private communication

C10H15O2- + Hydrogen cation = C10H16O2

By formula: C10H15O2- + H+ = C10H16O2

Quantity Value Units Method Reference Comment
Δr1435. ± 8.8kJ/molG+TSAdcock, Baran, et al., 2005gas phase; Entropy of acidity reassigned at 24 eu; authors did not take symmetry changes into account
Quantity Value Units Method Reference Comment
Δr1405. ± 8.4kJ/molCIDCAdcock, Baran, et al., 2005gas phase; Entropy of acidity reassigned at 24 eu; authors did not take symmetry changes into account

C9H15O2Si- + Hydrogen cation = C9H16O2Si

By formula: C9H15O2Si- + H+ = C9H16O2Si

Quantity Value Units Method Reference Comment
Δr1435. ± 8.8kJ/molG+TSAdcock, Baran, et al., 2005gas phase; Entropy of acidity reassigned at 24 eu; authors did not take symmetry changes into account
Quantity Value Units Method Reference Comment
Δr1405. ± 8.4kJ/molCIDCAdcock, Baran, et al., 2005gas phase; Entropy of acidity reassigned at 24 eu; authors did not take symmetry changes into account

C8H9O3- + Hydrogen cation = C8H10O3

By formula: C8H9O3- + H+ = C8H10O3

Quantity Value Units Method Reference Comment
Δr1419. ± 8.8kJ/molG+TSAdcock, Baran, et al., 2005gas phase; Entropy of acidity reassigned at 24 eu; authors did not take symmetry changes into account
Quantity Value Units Method Reference Comment
Δr1390. ± 8.4kJ/molCIDCAdcock, Baran, et al., 2005gas phase; Entropy of acidity reassigned at 24 eu; authors did not take symmetry changes into account

C6H6FO2- + Hydrogen cation = C6H7FO2

By formula: C6H6FO2- + H+ = C6H7FO2

Quantity Value Units Method Reference Comment
Δr1415. ± 8.8kJ/molG+TSAdcock, Baran, et al., 2005gas phase; Entropy of acidity reassigned at 24 eu; authors did not take symmetry changes into account
Quantity Value Units Method Reference Comment
Δr1385. ± 8.4kJ/molCIDCAdcock, Baran, et al., 2005gas phase; Entropy of acidity reassigned at 24 eu; authors did not take symmetry changes into account

C6H6ClO2- + Hydrogen cation = C6H7ClO2

By formula: C6H6ClO2- + H+ = C6H7ClO2

Quantity Value Units Method Reference Comment
Δr1409. ± 8.8kJ/molG+TSAdcock, Baran, et al., 2005gas phase; Entropy of acidity reassigned at 24 eu; authors did not take symmetry changes into account
Quantity Value Units Method Reference Comment
Δr1379. ± 8.4kJ/molCIDCAdcock, Baran, et al., 2005gas phase; Entropy of acidity reassigned at 24 eu; authors did not take symmetry changes into account

C7H6F3O2- + Hydrogen cation = C7H7F3O2

By formula: C7H6F3O2- + H+ = C7H7F3O2

Quantity Value Units Method Reference Comment
Δr1407. ± 8.8kJ/molG+TSAdcock, Baran, et al., 2005gas phase; Entropy of acidity reassigned at 24 eu; authors did not take symmetry changes into account
Quantity Value Units Method Reference Comment
Δr1377. ± 8.4kJ/molCIDCAdcock, Baran, et al., 2005gas phase; Entropy of acidity reassigned at 24 eu; authors did not take symmetry changes into account

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.

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McIver Jr.; Fukuda, E.K., Equilibrium Electron Affinities, Lec. Notes in Chem., 1982, 31, 165. [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]

Broadus and Kass, 1999
Broadus, K.M.; Kass, S.R., Benzocyclobutenone enolate: an anion with an antiaromatic resonance structure, J. Chem. Soc. Perkin Trans., 1999, 2, 11, 2389-2396, https://doi.org/10.1039/a905868k . [all data]

Adcock, Baran, et al., 2005
Adcock, W.; Baran, Y.; Filippi, A.; Speranza, M.; Trout, N.A., Polar substituent effects in the bicyclo[1.1.1]pentane ring system: Acidities of 3-substituted bicyclo[1.1.1]pentane-1-carboxylic acids, J. Org. Chem., 2005, 70, 3, 1029-1034, https://doi.org/10.1021/jo040236b . [all data]


Notes

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