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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
Deltar1475. ± 8.8kJ/molG+TSTaft and Topsom, 1987gas phase; value altered from reference due to change in acidity scale
Deltar1477. ± 10.kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1445. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase; value altered from reference due to change in acidity scale
Deltar1447. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C19H15- + Hydrogen cation = Triphenylmethane

By formula: C19H15- + H+ = C19H16

Quantity Value Units Method Reference Comment
Deltar1501. ± 9.2kJ/molG+TSTaft and Bordwell, 1988gas phase
Deltar1510. ± 10.kJ/molG+TSBartmessgas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1467. ± 8.4kJ/molIMRETaft and Bordwell, 1988gas phase
Deltar1476. ± 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
Deltar1653. ± 8.4kJ/molD-EARadisic, Xu, et al., 2002gas phase; BDE supported by 72GOL/SOL, over McMillen and Golden, 1982
Deltar1658.7 ± 3.7kJ/molG+TSMacKay, Hemsworth, et al., 1976gas phase
Quantity Value Units Method Reference Comment
Deltar1623. ± 8.8kJ/molH-TSRadisic, Xu, et al., 2002gas phase; BDE supported by 72GOL/SOL, over McMillen and Golden, 1982
Deltar1628.4 ± 2.5kJ/molIMREMacKay, Hemsworth, et al., 1976gas phase

CNS- + Hydrogen cation = Isothiocyanic acid

By formula: CNS- + H+ = CHNS

Quantity Value Units Method Reference Comment
Deltar<1361. ± 4.6kJ/molD-EABradforth, Kim, et al., 1993gas phase; Acid HNCS. HSCN up by ca. 8 kcal/mol
Deltar1375. ± 21.kJ/molG+TSBierbaum, Grabowski, et al., 1984gas phase; Acid: HNCS
Quantity Value Units Method Reference Comment
Deltar<1329. ± 5.9kJ/molH-TSBradforth, Kim, et al., 1993gas phase; Acid HNCS. HSCN up by ca. 8 kcal/mol
Deltar1343. ± 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
Deltar1538. ± 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
Deltar1507. ± 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
Deltar1461. ± 8.8kJ/molG+TSTaft, 1987gas phase; value altered from reference due to change in acidity scale
Deltar1466. ± 15.kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1431. ± 8.4kJ/molIMRETaft, 1987gas phase; value altered from reference due to change in acidity scale
Deltar1436. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C6H2N3O7- + Hydrogen cation = Picric acid

By formula: C6H2N3O7- + H+ = C6H3N3O7

Quantity Value Units Method Reference Comment
Deltar1298. ± 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
Deltar1267. ± 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.
Deltar<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
Deltar1317. ± 13.kJ/molD-EAWang, Broadus, et al., 2000gas phase; Vertical Detachment Energy: 5.02±0.05 eV
Deltar1304. ± 21.kJ/molG+TSBroadus and Kass, 2000gas phase
Quantity Value Units Method Reference Comment
Deltar1286. ± 14.kJ/molH-TSWang, Broadus, et al., 2000gas phase; Vertical Detachment Energy: 5.02±0.05 eV
Deltar1273. ± 21.kJ/molIMRBBroadus and Kass, 2000gas phase

CNO- + Hydrogen cation = Isocyanic acid

By formula: CNO- + H+ = CHNO

Quantity Value Units Method Reference Comment
Deltar1427.5 ± 2.6kJ/molD-EABradforth, Kim, et al., 1993gas phase; D-EA cycle requires a DH ca 4 kcal/mol weaker
Deltar1442. ± 8.8kJ/molG+TSWight and Beauchamp, 1980gas phase
Quantity Value Units Method Reference Comment
Deltar1400.6 ± 3.0kJ/molH-TSBradforth, Kim, et al., 1993gas phase; D-EA cycle requires a DH ca 4 kcal/mol weaker
Deltar1415. ± 8.4kJ/molIMREWight and Beauchamp, 1980gas phase

CClF2- + Hydrogen cation = Difluorochloromethane

By formula: CClF2- + H+ = CHClF2

Quantity Value Units Method Reference Comment
Deltar>1567.8kJ/molAcidPaulino and Squires, 1991gas phase; Probably CF2..Cl-, non-covalent.
Deltar1583. ± 29.kJ/molD-EADispert and Lacmann, 1978gas phase; From CF2Cl2
Quantity Value Units Method Reference Comment
Deltar>1535.4 ± 3.7kJ/molH-TSPaulino and Squires, 1991gas phase; Probably CF2..Cl-, non-covalent.
Deltar1550. ± 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
Deltar1628. ± 8.8kJ/molG+TSGal, Decouzon, et al., 2001gas phase; Acid: MeC«equiv»CMe
Deltar1628. ± 14.kJ/molG+TSN/Agas phase; Measured vs pyridine
Quantity Value Units Method Reference Comment
Deltar1597. ± 8.4kJ/molIMREGal, Decouzon, et al., 2001gas phase; Acid: MeC«equiv»CMe
Deltar1596. ± 13.kJ/molIMREN/Agas phase; Measured vs pyridine

thiophenoxide anion + Hydrogen cation = Benzenethiol

By formula: C6H5S- + H+ = C6H6S

Quantity Value Units Method Reference Comment
Deltar1424. ± 8.8kJ/molG+TSTaft and Bordwell, 1988gas phase
Deltar>1423. ± 7.5kJ/molD-EARichardson, Stephenson, et al., 1975gas phase
Quantity Value Units Method Reference Comment
Deltar1395. ± 8.8kJ/molIMREGuillemin, Riague, et al., 2005gas phase
Deltar1397. ± 8.4kJ/molIMRETaft and Bordwell, 1988gas phase
Deltar>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
Deltar1426. ± 8.8kJ/molG+TSMishima, Matsuoka, et al., 2004gas phase; Calc: keto form of acid more stable.
Deltar1425. ± 8.8kJ/molG+TSTaft, Abboud, et al., 1988gas phase
Quantity Value Units Method Reference Comment
Deltar1400. ± 8.4kJ/molIMREMishima, Matsuoka, et al., 2004gas phase; Calc: keto form of acid more stable.
Deltar1399. ± 8.4kJ/molIMRETaft, Abboud, et al., 1988gas phase

C2F3O- + Hydrogen cation = C2HF3O

By formula: C2F3O- + H+ = C2HF3O

Quantity Value Units Method Reference Comment
Deltar>1623. ± 17.kJ/molD-EAHarland and Thynne, 1970gas phase; From (CF3)2CO. Values unreasonable: «DELTA»Hf(CF3CO-)must be less than «DELTA»Hf(CF3-+CO)=-181. G3MP2B3 EA = 1.6 eV
Quantity Value Units Method Reference Comment
Deltar>1590. ± 17.kJ/molH-TSHarland and Thynne, 1970gas phase; From (CF3)2CO. Values unreasonable: «DELTA»Hf(CF3CO-)must be less than «DELTA»Hf(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
Deltar1555. ± 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
Deltar1523. ± 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
Deltar1503.6kJ/molAcidPoutsma, Paulino, et al., 1997gas phase
Deltar1507. ± 8.8kJ/molG+TSPoutsma, Paulino, et al., 1997gas phase
Deltar<1506. ± 20.kJ/molD-EAIllenberger, Baumgartel, et al., 1979gas phase; From CF2Cl2
Quantity Value Units Method Reference Comment
Deltar1471.2 ± 2.5kJ/molH-TSPoutsma, Paulino, et al., 1997gas phase
Deltar1475. ± 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
Deltar1515. ± 10.kJ/molG+TSBartmess and Griffiths, 1990gas phase; Isomer 9-methylene-9,10-dihydroanthracene: «DELTA»G=349.0±3.0, «DELTA»S=27.0, «DELTA»H=357.1;DH: Zhang, Bordwell, et al., 1993
Quantity Value Units Method Reference Comment
Deltar1486. ± 9.6kJ/molIMREBartmess and Griffiths, 1990gas phase; Isomer 9-methylene-9,10-dihydroanthracene: «DELTA»G=349.0±3.0, «DELTA»S=27.0, «DELTA»H=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
Deltar1427. ± 8.8kJ/molG+TSKebarle and McMahon, 1977gas phase
Deltar1425. ± 8.8kJ/molG+TSDecouzon, Exner, et al., 1996gas phase; relative to benzoate at 333.0 kcal/mol
Quantity Value Units Method Reference Comment
Deltar1397. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase
Deltar1396. ± 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
Deltar1425. ± 8.8kJ/molG+TSKebarle and McMahon, 1977gas phase
Deltar1424. ± 8.8kJ/molG+TSDecouzon, Exner, et al., 1996gas phase; Relative to benzoate at 333.0 kcal/mol
Quantity Value Units Method Reference Comment
Deltar1396. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase
Deltar1395. ± 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
Deltar1630. ± 13.kJ/molD-EARackwitz, Feldman, et al., 1977gas phase; «DELTA»Hf(BeH2){ Chase Jr., Davies, et al., 1985} is 1959 SWAG. G3(MP2)calcn(JEB): «DELTA»Hf=44.5kcal, BDE=92.1, «DELTA»Hacid=389.7
Quantity Value Units Method Reference Comment
Deltar1595. ± 13.kJ/molH-TSRackwitz, Feldman, et al., 1977gas phase; «DELTA»Hf(BeH2){ Chase Jr., Davies, et al., 1985} is 1959 SWAG. G3(MP2)calcn(JEB): «DELTA»Hf=44.5kcal, BDE=92.1, «DELTA»Hacid=389.7

CHF2- + Hydrogen cation = Difluoromethane

By formula: CHF2- + H+ = CH2F2

Quantity Value Units Method Reference Comment
Deltar1628. ± 15.kJ/molCIDTGraul and Squires, 1990gas phase; G2 calculations( Lee, Dyke, et al., 1998) predict «DELTA»Hacid = 399 kcal/mol
Quantity Value Units Method Reference Comment
Deltar1595. ± 15.kJ/molH-TSGraul and Squires, 1990gas phase; G2 calculations( Lee, Dyke, et al., 1998) predict «DELTA»Hacid = 399 kcal/mol
Deltar1586. ± 25.kJ/molIMRBSullivan, 1977gas phase

Carbon anion + Hydrogen cation = C2H

By formula: C2- + H+ = C2H

Quantity Value Units Method Reference Comment
Deltar>1460. ± 15.kJ/molD-EAArnold, Bradforth, et al., 1991gas phase
Deltar<1572. ± 9.6kJ/molG+TSSchiff and Bohme, 1975gas phase; No reaction with acetylene
Quantity Value Units Method Reference Comment
Deltar>1430. ± 16.kJ/molH-TSArnold, Bradforth, et al., 1991gas phase
Deltar<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
Deltar1576. ± 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
Deltar1544. ± 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
Deltar1451. ± 8.4kJ/molTDEqNorrman and McMahon, 1999gas phase
Deltar1450. ± 9.2kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Deltar1450. ± 9.2kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1420. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase
Deltar1420. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C3H7- + Hydrogen cation = Propane

By formula: C3H7- + H+ = C3H8

Quantity Value Units Method Reference Comment
Deltar1755. ± 8.4kJ/molBranDePuy, Gronert, et al., 1989gas phase
Deltar1755. ± 20.kJ/molBranPeerboom, Rademaker, et al., 1992gas phase
Deltar1753. ± 8.4kJ/molBranDePuy, Bierbaum, et al., 1984gas phase
Quantity Value Units Method Reference Comment
Deltar1721. ± 8.8kJ/molH-TSDePuy, Gronert, et al., 1989gas phase
Deltar1722. ± 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
Deltar1471. ± 13.kJ/molG+TSDownard, Bowie, et al., 1992gas phase; Acid: between CF3COCH3, tBuSH
Deltar1471. ± 17.kJ/molD-EAMoran and Ellison, 1988gas phase
Quantity Value Units Method Reference Comment
Deltar1443. ± 13.kJ/molIMRBDownard, Bowie, et al., 1992gas phase; Acid: between CF3COCH3, tBuSH
Deltar1443. ± 17.kJ/molH-TSMoran and Ellison, 1988gas phase

C7H6NO2 + Hydrogen cation = Trigonelline

By formula: C7H6NO2 + H+ = C7H7NO2

Quantity Value Units Method Reference Comment
Deltar1507. ± 21.kJ/molD-EAWang, Broadus, et al., 2000gas phase; ArCO2-: EAad = 3.8±0.1 eV
Deltar1448. ± 21.kJ/molG+TSBroadus and Kass, 2000gas phase
Quantity Value Units Method Reference Comment
Deltar1474. ± 21.kJ/molH-TSWang, Broadus, et al., 2000gas phase; ArCO2-: EAad = 3.8±0.1 eV
Deltar1415. ± 21.kJ/molIMRBBroadus and Kass, 2000gas phase

C5H9O- + Hydrogen cation = Cyclopentanol

By formula: C5H9O- + H+ = C5H10O

Quantity Value Units Method Reference Comment
Deltar1602. ± 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
Deltar1535. ± 4.6kJ/molN/AGarver, Yang, et al., 2011gas phase
Deltar1569. ± 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
Deltar1612. ± 10.kJ/molTDEqMeot-ner and Kafafi, 1988gas phase; Acid: pyrimidine. Anchored to 88MEO scale, not "87 acidity scale
Quantity Value Units Method Reference Comment
Deltar1576.5 ± 2.9kJ/molN/AWren, Vogelhuber, et al., 2012gas phase
Deltar1577. ± 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
Deltar1600. ± 10.kJ/molTDEqMeot-ner and Kafafi, 1988gas phase; Pyridazine. Anchored to 88MEO scale, not the "87 Acidity Scale".
Quantity Value Units Method Reference Comment
Deltar1564.8 ± 2.9kJ/molN/AWren, Vogelhuber, et al., 2012gas phase
Deltar1562. ± 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
Deltar1594. ± 8.8kJ/molD-EABrinkman, Berger, et al., 1994gas phase
Deltar1610. ± 17.kJ/molG+TSDamrauer, Kass, et al., 1988gas phase; Between furan and methanol.
Quantity Value Units Method Reference Comment
Deltar1561. ± 9.2kJ/molH-TSBrinkman, Berger, et al., 1994gas phase
Deltar1577. ± 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
Deltar1399. ± 8.4kJ/molCIDCSchafman and Wenthold, 2007gas phase
Deltar1395. ± 12.kJ/molG+TSBreuker, Knochenmuss, et al., 1999gas phase; Acid: nicotinic acid
Quantity Value Units Method Reference Comment
Deltar1370. ± 9.2kJ/molH-TSSchafman and Wenthold, 2007gas phase
Deltar1366. ± 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
Deltar1497. ± 9.2kJ/molG+TSGrimm and Bartmess, 1992gas phase
Deltar1504. ± 17.kJ/molG+TSDamrauer, Simon, et al., 1991gas phase; between pyrrole, CF3CH2OH
Quantity Value Units Method Reference Comment
Deltar1471. ± 8.4kJ/molIMREGrimm and Bartmess, 1992gas phase
Deltar1477. ± 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
Deltar1492. ± 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
Deltar1461. ± 15.kJ/molIMRBMcDonald, Chowdhury, et al., 1987gas phase; Acidity between MeNO2, EtSH. Acid taken as (MeO)2P(O)H.
Deltar1469. ± 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
Deltar<1606.7kJ/molCIDTGraul and Squires, 1988gas phase
Deltar<1639.1 ± 3.8kJ/molG+TSDePuy, Grabowski, et al., 1985gas phase; HO- + DCO2CH3 -> (M-D)-. «DELTA»Hf(MeO- + CO) = -59.7 kcal/mol
Quantity Value Units Method Reference Comment
Deltar<1606.7kJ/molIMRBDePuy, Grabowski, et al., 1985gas phase; HO- + DCO2CH3 -> (M-D)-. «DELTA»Hf(MeO- + CO) = -59.7 kcal/mol

CHN2- + Hydrogen cation = 3H-Diazirine

By formula: CHN2- + H+ = CH2N2

Quantity Value Units Method Reference Comment
Deltar1681. ± 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
Deltar1648. ± 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
Deltar1564. ± 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
Deltar1533. ± 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
Deltar1593. ± 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
Deltar1565. ± 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
Deltar1515. ± 8.8kJ/molG+TSDecouzon, Exner, et al., 1990gas phase; value altered from reference due to change in acidity scale
Deltar1500. ± 5.0kJ/molEIAEMuftakhov, Vasil'ev, et al., 1999gas phase
Quantity Value Units Method Reference Comment
Deltar1485. ± 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
Deltar1412. ± 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
Deltar1384. ± 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
Deltar1400. ± 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
Deltar1370. ± 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
Deltar1654. ± 11.kJ/molG+TSKass, Guo, et al., 1990gas phase; Acidity between D2O and Me2NH.
Deltar1638. ± 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
Deltar1624. ± 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
Deltar1466. ± 8.8kJ/molG+TSGal, Decouzon, et al., 2001gas phase
Deltar1461.9kJ/molN/ACheck, Faust, et al., 2001gas phase; NiH2; ; «DELTA»S(EA)=10.0
Quantity Value Units Method Reference Comment
Deltar1432. ± 8.4kJ/molIMREGal, Decouzon, et al., 2001gas phase
Deltar1428.4kJ/molN/ACheck, Faust, et al., 2001gas phase; NiH2; ; «DELTA»S(EA)=10.0

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

By formula: C8H5O- + H+ = C8H6O

Quantity Value Units Method Reference Comment
Deltar1505. ± 9.2kJ/molG+TSBroadus and Kass, 1999gas phase; Correction to direction of «DELTA»Gacid reported in literature: Kass, private communication
Quantity Value Units Method Reference Comment
Deltar1473. ± 8.8kJ/molIMREBroadus and Kass, 1999gas phase; Correction to direction of «DELTA»Gacid reported in literature: Kass, private communication

C10H15O2- + Hydrogen cation = C10H16O2

By formula: C10H15O2- + H+ = C10H16O2

Quantity Value Units Method Reference Comment
Deltar1435. ± 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
Deltar1405. ± 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
Deltar1435. ± 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
Deltar1405. ± 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
Deltar1419. ± 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
Deltar1390. ± 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
Deltar1415. ± 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
Deltar1385. ± 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
Deltar1409. ± 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
Deltar1379. ± 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
Deltar1407. ± 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
Deltar1377. ± 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.

Taft and Topsom, 1987
Taft, R.W.; Topsom, R.D., The Nature and Analysis of Substituent Effects, Prog. Phys. Org. Chem., 1987, 16, 1. [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 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]

Bartmess
Bartmess, J.E., The Gas Phase Thermochemistry of Ph3C-, Ph3C., and Ph3C+, 32nd Ann. Conf. on Mass Spectrom. Allied Topics, San Antonio TX 27 May-1 June 1984. Abstracts p. 472. [all data]

Radisic, Xu, et al., 2002
Radisic, D.; Xu, S.J.; Bowen, K.H., Photoelectron spectroscopy of the anions, CH3NH- and (CH3)(2)N- and the anion complexes, H-(CH3NH2) and (CH3)(2)N-[(CH3)(2)NH), Chem. Phys. Lett., 2002, 354, 1-2, 9-13, https://doi.org/10.1016/S0009-2614(01)01470-1 . [all data]

McMillen and Golden, 1982
McMillen, D.F.; Golden, D.M., Hydrocarbon bond dissociation energies, Ann. Rev. Phys. Chem., 1982, 33, 493. [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]

Bradforth, Kim, et al., 1993
Bradforth, S.E.; Kim, E.H.; Arnold, D.W.; Neumark, D.M., Photoelectron Spectroscopy of CN-, NCO-, and NCS-, J. Chem. Phys., 1993, 98, 2, 800, https://doi.org/10.1063/1.464244 . [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]

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]

Taft, 1987
Taft, R.W., The Nature and Analysis of Substitutent Electronic Effects, Personal communication. See also Prog. Phys. Org. Chem., 1987, 16, 1. [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]

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]

Dzidic, Carroll, et al., 1974
Dzidic, I.; Carroll, D.I.; Stillwell, R.N.; Horning, E.C., Gas phase reactions. Ionization by proton transfer to superoxide anions, J. Am. Chem. Soc., 1974, 96, 5258. [all data]

Wang, Broadus, et al., 2000
Wang, X.B.; Broadus, K.M.; Wang, L.S.; Kass, S.R., Photodetachment of the first zwitterionic anions in the gas phase: Probing intramolecular Coulomb repulsion and attraction, J. Am. Chem. Soc., 2000, 122, 34, 8305-8306, https://doi.org/10.1021/ja001943z . [all data]

Broadus and Kass, 2000
Broadus, K.M.; Kass, S.R., Probing Electrostatic Effects: Formation and Characterization of Zwitterionic Ions and their Neutral Counterparts in the Gas Phase, J. Am. Chem. Soc., 2000, 122, 37, 9014, https://doi.org/10.1021/ja0016708 . [all data]

Wight and Beauchamp, 1980
Wight, C.A.; Beauchamp, J.L., Acidity, basicity, and ion/molecule reactions of isocyanic acid in the gas phase by ICR spectroscopy, J. Phys. Chem., 1980, 84, 2503. [all data]

Paulino and Squires, 1991
Paulino, J.A.; Squires, R.R., Carbene Anion Complexes - Unusual Structural and Thermochemical Features of alpha-Halocarbanions in the Gas Phase, J. Am. Chem. Soc., 1991, 113, 5, 1845, https://doi.org/10.1021/ja00005a067 . [all data]

Dispert and Lacmann, 1978
Dispert, H.; Lacmann, K., Negative ion formation in collisions between potassium and fluoro- and chloromethanes: Electron affinities and bond dissociation energies, Int. J. Mass Spectrom. Ion Phys., 1978, 28, 49. [all data]

Gal, Decouzon, et al., 2001
Gal, J.F.; Decouzon, M.; Maria, P.C.; Gonzalez, A.I.; Mo, O.; Yanez, M.; El Chaouch, S.; Guillemin, J.C., Acidity trends in alpha,beta-unsaturated alkanes, silanes, germanes, and stannanes, J. Am. Chem. Soc., 2001, 123, 26, 6353-6359, https://doi.org/10.1021/ja004079j . [all data]

Richardson, Stephenson, et al., 1975
Richardson, J.H.; Stephenson, L.M.; Brauman, J.I., Photodetachment of electrons from phenoxides and thiophenoxide, J. Am. Chem. Soc., 1975, 97, 2967. [all data]

Guillemin, Riague, et al., 2005
Guillemin, J.C.; Riague, E.H.; Gal, J.F.; Maria, P.C.; Mo, O.; Yanez, M., Acidity trends in alpha,beta-unsaturated sulfur, selenium, and tellurium derivatives: Comparison with C-, Si-, Ge-, Sn-, N-, P-, As-, and Sb-containing analogues, Chem. Eur. J., 2005, 11, 7, 2145-2153, https://doi.org/10.1002/chem.200400989 . [all data]

Mishima, Matsuoka, et al., 2004
Mishima, M.; Matsuoka, M.; Lei, Y.X.; Rappoport, Z., Gas-phase acidities of disubstituted methanes and of enols of carboxamides substituted by electron-withdrawing groups, J. Org. Chem., 2004, 69, 18, 5947-5965, https://doi.org/10.1021/jo040196b . [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]

Harland and Thynne, 1970
Harland, P.; Thynne, J.C.J., Positive and negative ion formation in hexafluoroacetone by electron impact, J. Phys. Chem., 1970, 74, 52. [all data]

Chabinyc and Brauman, 1999
Chabinyc, M.L.; Brauman, J.I., Hydrogen bond strength and acidity. Structural and energetic correlations for acetylides and alcohols, J. Phys. Chem. A, 1999, 103, 46, 9163-9166, https://doi.org/10.1021/jp992852v . [all data]

Poutsma, Paulino, et al., 1997
Poutsma, J.C.; Paulino, J.A.; Squires, R.R., Absolute Heats of Formation of CHCl, CHF, and CClF. A Gas-Phase Experimental and G2 Theoretical Study., J. Phys. Chem. A, 1997, 101, 29, 5327, https://doi.org/10.1021/jp970778f . [all data]

Illenberger, Baumgartel, et al., 1979
Illenberger, T.; Baumgartel, H.; Scheunemann, H., Negative Ion Formation in CF2Cl2, CF3Cl, and CFCl3 Following Low Energy (0-10eV) Impact with Near Monoenergetic Electrons, Chem. Phys., 1979, 37, 1, 21, https://doi.org/10.1016/0301-0104(79)80003-8 . [all data]

Bartmess and Griffiths, 1990
Bartmess, J.E.; Griffiths, S.S., Tautomerization Energetics of Benzoannelated Toluenes, J. Am. Chem. Soc., 1990, 112, 8, 2932, https://doi.org/10.1021/ja00164a014 . [all data]

Zhang, Bordwell, et al., 1993
Zhang, X.M.; Bordwell, F.G.; Bares, J.E.; Cheng, J.P.; Petrie, B.C., Homolytic Bond Dissociation Energies of the Acidic C-H Bonds in alpha-Substituted and 10-Substituted 9-Methylanthracenes and Their Related Radical Anions, J. Org. Chem., 1993, 58, 11, 3051, https://doi.org/10.1021/jo00063a025 . [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]

Decouzon, Exner, et al., 1996
Decouzon, M.; Exner, O.; Gal, J.-F.; Maria, P.-C., Non-classical Buttressing Effect: Gas-phase Ionization of Some Methyl Substituted Benzoic Acids, J. Chem. Soc. Perkin Trans., 1996, 2, 4, 475, https://doi.org/10.1039/p29960000475 . [all data]

Rackwitz, Feldman, et al., 1977
Rackwitz, R.; Feldman, D.; Kaiser, H.J.; Heincke, E., Photodetachment bei einigen zweiatomigen negativen hydridionen: BeH-, MgH-, CaH-, ZnH-, PH-, AsH-, Z. Naturforsch. A:, 1977, 32, 594. [all data]

Chase Jr., Davies, et al., 1985
Chase Jr.; Davies, C.A.; Downey Jr.; Frurip, D.J.; McDonald, R.A.; Syverud, A.N., JANAF Thermochemical Tables (Third Edition), J. Phys. Chem. Ref. Data, Suppl. 1, 1985, 14. [all data]

Graul and Squires, 1990
Graul, S.T.; Squires, R.R., Gas-Phase Acidities Derived from Threshold Energies for Activated Reactions, J. Am. Chem. Soc., 1990, 112, 7, 2517, https://doi.org/10.1021/ja00163a007 . [all data]

Lee, Dyke, et al., 1998
Lee, E.P.F.; Dyke, J.M.; Mayhew, C.A., Study of the OH-+CH2F2 reaction by selected ion flow tube experiments and ab initio calculations, J. Phys. Chem. A, 1998, 102, 43, 8349-8354, https://doi.org/10.1021/jp982224y . [all data]

Sullivan, 1977
Sullivan, S.A., Thesis, Cal. Inst. Tech. thesis,, 1977. [all data]

Arnold, Bradforth, et al., 1991
Arnold, D.W.; Bradforth, S.E.; Kitsopoulos, T.N.; Neumark, D.M., Vibrationally Resolved Spectra of C2-C11 by Anion Photoelectron Spectroscopy, J. Chem. Phys., 1991, 95, 12, 8753, https://doi.org/10.1063/1.461211 . [all data]

Schiff and Bohme, 1975
Schiff, H.I.; Bohme, D.K., Flowing afterglow studies at York University, Int. J. Mass Spectrom. Ion Phys., 1975, 16, 167. [all data]

Kleingeld and Nibbering, 1984
Kleingeld, J.C.; Nibbering, N.M.M., Negative Ion/Molecule Cycloaddition Reactions of 2-Methylpropenal in the Gas Phase, Recl. Trav. Chim. Pays-Bas, 1984, 103, 3, 87, https://doi.org/10.1002/recl.19841030303 . [all data]

Norrman and McMahon, 1999
Norrman, K.; McMahon, T.B., Intramolecular solvation of carboxylate anions in the gas phase, J. Phys. Chem. A, 1999, 103, 35, 7008-7016, https://doi.org/10.1021/jp9908202 . [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]

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]

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]

DePuy, Bierbaum, et al., 1984
DePuy, C.H.; Bierbaum, V.M.; Damrauer, R., Relative Gas-Phase Acidities of the Alkanes, J. Am. Chem. Soc., 1984, 106, 4051. [all data]

Downard, Bowie, et al., 1992
Downard, K.M.; Bowie, J.H.; O'Hair, R.A.J.; Krempp, M.; DePuy, C.H., Gas Phase Reactions of the Methylsulfinyl and Methyldisulfide Anions, Int. J. Mass Spectrom. Ion Proc., 1992, 120, 3, 217, https://doi.org/10.1016/0168-1176(92)85050-A . [all data]

Moran and Ellison, 1988
Moran, S.; Ellison, G.B., Photoelectron Spectroscopy of Sulfur Ions, J. Phys. Chem., 1988, 92, 7, 1794, https://doi.org/10.1021/j100318a021 . [all data]

Alconcel and Continetti, 2002
Alconcel, L.S.; Continetti, R.E., Dissociation dynamics and stability of cyclopentoxy and cyclopentoxide, Chem. Phys. Lett., 2002, 366, 5-6, 642-649, https://doi.org/10.1016/S0009-2614(02)01633-0 . [all data]

Garver, Yang, et al., 2011
Garver, J.M.; Yang, Z.B.; Kato, S.; Wren, S.W.; Vogelhuber, K.M.; Lineberger, W.C.; Bierbaum, V.M., Gas Phase Reactions of 1,3,5-Triazine: Proton Transfer, Hydride Transfer, and Anionic sigma-Adduct Formation, J. Am. Soc. Mass Spectrom., 2011, 22, 7, 1260-1272, https://doi.org/10.1007/s13361-011-0133-9 . [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]

Wren, Vogelhuber, et al., 2012
Wren, S.W.; Vogelhuber, K.M.; Garver, J.M.; Kato, S.; Sheps, L.; Bierbaum, V.M.; Lineberger, W.C., C-H Bond Strengths and Acidities in Aromatic Systems: Effects of Nitrogen Incorporation in Mono-, Di-, and Triazines, J. Am. Chem. Soc., 2012, 134, 15, 6584-6595, https://doi.org/10.1021/ja209566q . [all data]

Brinkman, Berger, et al., 1994
Brinkman, E.A.; Berger, S.; Brauman, J.I., alpha-Silyl-substituent stabilization of carbanions and silyl anions, J. Am. Chem. Soc., 1994, 116, 18, 8304, https://doi.org/10.1021/ja00097a042 . [all data]

Damrauer, Kass, et al., 1988
Damrauer, R.; Kass, S.R.; DePuy, C.H., Gas-Phase Acidities of Methylsilanes: C-H versus Si-H, Organomet., 1988, 7, 3, 637, https://doi.org/10.1021/om00093a011 . [all data]

Schafman and Wenthold, 2007
Schafman, B.S.; Wenthold, P.G., Regioselectivity of pyridine deprotonation in the gas phase, J. Org. Chem., 2007, 72, 5, 1645-1651, https://doi.org/10.1021/jo062117x . [all data]

Breuker, Knochenmuss, et al., 1999
Breuker, K.; Knochenmuss, R.; Zenobi, R., Gas-phase basicities of deprotonated matrix-assisted laser desorption/ionization matrix molecules, Int. J. Mass Spectrom., 1999, 184, 1, 25-38, https://doi.org/10.1016/S1387-3806(98)14200-8 . [all data]

Grimm and Bartmess, 1992
Grimm, D.T.; Bartmess, J.E., The Intrinsic (Gas Phase) Basicity of some Anions Commonly Used in Condensed-Phase Synthesis, J. Am. Chem. Soc., 1992, 114, 4, 1227, https://doi.org/10.1021/ja00030a016 . [all data]

Damrauer, Simon, et al., 1991
Damrauer, R.; Simon, R.; Krempp, M., Effect of Substituents on the Gas-Phase Acidity of Silanols, J. Am. Chem. Soc., 1991, 113, 12, 4431, https://doi.org/10.1021/ja00012a009 . [all data]

McDonald, Chowdhury, et al., 1987
McDonald, R.M.; Chowdhury, A.K.; Gung, W.Y.; DeWitt, K.D., Nucleophilic Reactivity in Anionic Ion-Molecule Reactions in Nucleophilicity, Harris, J.M, McManus, S.P. Eds., Amer. Chem. Soc, 1987. [all data]

Anderson, DePuy, et al., 1984
Anderson, D.R.; DePuy, C.H.; Filley, J.; Bierbaum, V.M., Gas Phase Chemistry of Trimethyl Phosphite, J. Am. Chem. Soc., 1984, 106, 22, 6513, https://doi.org/10.1021/ja00334a009 . [all data]

Graul and Squires, 1988
Graul, S.T.; Squires, R.R., On the Existence of Alkyl Carbanions in the Gas Phase, J. Am. Chem. Soc., 1988, 110, 2, 607, https://doi.org/10.1021/ja00210a054 . [all data]

DePuy, Grabowski, et al., 1985
DePuy, C.H.; Grabowski, J.J.; Bierbaum, V.M.; Ingemann, S.; Nibbering, N.M.M., Gas-phase reactions of anions with methyl formate and N,N-dimethylformamide, J. Am. Chem. Soc., 1985, 107, 1093. [all data]

Kroeker and Kass, 1990
Kroeker, R.L.; Kass, S.R., Diazirinyl Anion: A Cyclic 4-pi Electron System, J. Am. Chem. Soc., 1990, 112, 24, 9024, https://doi.org/10.1021/ja00180a082 . [all data]

Srivastava, Uy, et al., 1974
Srivastava, R.D.; Uy, O.M.; Farber, M., Experimental determination of heats of formation of negative ions and electron affinities of several boron and aluminum fluorides, J. Chem. Soc. Faraday Trans. 1, 1974, 70, 1033. [all data]

Damrauer, DePuy, et al., 1986
Damrauer, R.; DePuy, C.H.; Davidson, I.M.T.; Hughes, K.J., Gas phase ion chemistry of dimethylsilylene, Organometallics, 1986, 5, 2054. [all data]

Decouzon, Exner, et al., 1990
Decouzon, M.; Exner, O.; Gal, J.-F.; Maria, P.-C., The Gas-Phase Acidity and the Acidic Site of Acetohydroxamic Acid: an FT-ICR Study, J. Org. Chem., 1990, 55, 13, 3980, https://doi.org/10.1021/jo00300a007 . [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]

Farid and McMahon, 1980
Farid, R.; McMahon, T.B., The gas phase acidities of fluorinated acetones. An ICR investigation of the role of fluorine substituents in the stabilization of planar carbanions, Can. J. Chem., 1980, 58, 2307. [all data]

Koppel, Pihl, et al., 1994
Koppel, I.A.; Pihl, V.; Koppel, I.A.; Anvia, F.; Taft, R.W., Thermodynamic acidity of (CF3)3CH and 1H-undecafluorobicyclo[2.2.1]heptane: The concept of anionic (fluorine) hyperconjugation, J. Am. Chem. Soc., 1994, 116, 19, 8654, https://doi.org/10.1021/ja00098a027 . [all data]

Burk, Koppel, et al., 2000
Burk, P.; Koppel, I.A.; Rummel, A.; Trummal, A., Can O-H acid be more acidic than its S-H analog? A G2 study of fluoromethanols and fluoromethanethiols, J. Phys. Chem. A, 2000, 104, 7, 1602-1607, https://doi.org/10.1021/jp993487a . [all data]

Kass, Guo, et al., 1990
Kass, S.R.; Guo, H.-Z.; Dahlke, G.D., The Thiomethyl Anion: Formation, Reactivity, and Thermodynamic Properties, J. Am. Soc. Mass Spectrom., 1990, 1, 5, 366, https://doi.org/10.1016/1044-0305(90)85016-F . [all data]

McIver Jr. and Fukuda, 1982
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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