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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 151 to 200

C13H9- + Hydrogen cation = Fluorene

By formula: C13H9- + H+ = C13H10

Quantity Value Units Method Reference Comment
Deltar1466. ± 8.4kJ/molD-EARömer, Janaway, et al., 1997gas phase
Deltar1472. ± 8.8kJ/molG+TSTaft and Bordwell, 1988gas phase
Deltar1478. ± 11.kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1434. ± 8.8kJ/molH-TSRömer, Janaway, et al., 1997gas phase
Deltar1439. ± 8.4kJ/molIMRETaft and Bordwell, 1988gas phase
Deltar1446. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C3H5O2- + Hydrogen cation = Acetic acid, methyl ester

By formula: C3H5O2- + H+ = C3H6O2

Quantity Value Units Method Reference Comment
Deltar1556. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Deltar1556. ± 15.kJ/molD-EAZimmerman, Reed, et al., 1977gas phase
Deltar1573. ± 15.kJ/molEIAEPariat and Allan, 1991gas phase; From CH3CO2Me
Quantity Value Units Method Reference Comment
Deltar1528. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale

C6H6N- + Hydrogen cation = Aniline

By formula: C6H6N- + H+ = C6H7N

Quantity Value Units Method Reference Comment
Deltar1540.5 ± 1.3kJ/molD-EAWren, Vogelhuber, et al., 2012gas phase
Deltar1533. ± 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
Deltar1510.0 ± 2.8kJ/molH-TSWren, Vogelhuber, et al., 2012gas phase
Deltar1502. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale

C4H11Si- + Hydrogen cation = Silane, tetramethyl-

By formula: C4H11Si- + H+ = C4H12Si

Quantity Value Units Method Reference Comment
Deltar1624. ± 13.kJ/molG+TSDamrauer, Kass, et al., 1988gas phase; Comparable to fluorobenzene
Deltar1636. ± 8.4kJ/molD-EAWetzel and Brauman, 1988gas phase
Quantity Value Units Method Reference Comment
Deltar1586. ± 13.kJ/molIMRBDamrauer, Kass, et al., 1988gas phase; Comparable to fluorobenzene
Deltar1597. ± 8.8kJ/molH-TSWetzel and Brauman, 1988gas phase
Deltar1635. ± 21.kJ/molIMRBDePuy and Damrauer, 1984gas phase

MeS anion + Hydrogen cation = Methanethiol

By formula: CH3S- + H+ = CH4S

Quantity Value Units Method Reference Comment
Deltar1496. ± 8.4kJ/molD-EASchwartz, Davico, et al., 2000gas phase
Deltar1496. ± 8.4kJ/molD-EAMoran and Ellison, 1988gas phase
Deltar1493. ± 9.2kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1467. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale

C3H3N2- + Hydrogen cation = 1H-Pyrazole

By formula: C3H3N2- + H+ = C3H4N2

Quantity Value Units Method Reference Comment
Deltar1479. ± 10.kJ/molG+TSGianola, Ichino, et al., 2006gas phase
Deltar1479. ± 10.kJ/molG+TSTaft, Anvia, et al., 1986gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1449. ± 9.6kJ/molN/AGianola, Ichino, et al., 2006gas phase
Deltar1449. ± 9.6kJ/molIMRETaft, Anvia, et al., 1986gas phase; value altered from reference due to change in acidity scale

C2HClN- + Hydrogen cation = Chloromethyl cyanide

By formula: C2HClN- + H+ = C2H2ClN

Quantity Value Units Method Reference Comment
Deltar1497. ± 9.2kJ/molG+TSPoutsma, Upshaw, et al., 2002gas phase
Deltar1457. ± 29.kJ/molEIAEHacaloglu, Suzer, et al., 1988gas phase; From ClCH2CN. «DELTA»Gacid more likely to be ca. 360 - JEB.
Quantity Value Units Method Reference Comment
Deltar1464. ± 8.4kJ/molIMRBPoutsma, Upshaw, et al., 2002gas phase
Deltar1429. ± 33.kJ/molH-TSHacaloglu, Suzer, et al., 1988gas phase; From ClCH2CN. «DELTA»Gacid more likely to be ca. 360 - JEB.

C9H11O- + Hydrogen cation = p-Cumenol

By formula: C9H11O- + H+ = C9H12O

Quantity Value Units Method Reference Comment
Deltar1461. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; «DELTA»Hf(AH) disagrees with group additivity by 8.6 kcal/mol (-41.4 kcal/mol; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1433. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; «DELTA»Hf(AH) disagrees with group additivity by 8.6 kcal/mol (-41.4 kcal/mol; value altered from reference due to change in acidity scale

C7H15O- + Hydrogen cation = 2-Hexanol, 2-methyl-

By formula: C7H15O- + H+ = C7H16O

Quantity Value Units Method Reference Comment
Deltar1555. ± 8.8kJ/molG+TSHiggins and Bartmess, 1998gas phase
Deltar1555. ± 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
Deltar1528. ± 8.4kJ/molIMREHiggins and Bartmess, 1998gas phase
Deltar1527. ± 11.kJ/molCIDCBoand, Houriet, et al., 1983gas phase; value altered from reference due to change in acidity scale

C6H4FO- + Hydrogen cation = Phenol, 2-fluoro-

By formula: C6H4FO- + H+ = C6H5FO

Quantity Value Units Method Reference Comment
Deltar1445. ± 9.2kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1447. ± 12.kJ/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Deltar1418. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1420. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase

C6H5O2- + Hydrogen cation = 1,2-Benzenediol

By formula: C6H5O2- + H+ = C6H6O2

Quantity Value Units Method Reference Comment
Deltar1420. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1422. ± 11.kJ/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Deltar1392. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1393. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase

C7H4NO- + Hydrogen cation = Benzonitrile, 2-hydroxy-

By formula: C7H4NO- + H+ = C7H5NO

Quantity Value Units Method Reference Comment
Deltar1400. ± 9.2kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1400. ± 12.kJ/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Deltar1369. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1369. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase

C6H6NO- + Hydrogen cation = Phenol, 3-amino-

By formula: C6H6NO- + H+ = C6H7NO

Quantity Value Units Method Reference Comment
Deltar1466. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1469. ± 9.6kJ/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Deltar1438. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1441. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase

C6H6NO- + Hydrogen cation = Phenol, 4-amino-

By formula: C6H6NO- + H+ = C6H7NO

Quantity Value Units Method Reference Comment
Deltar1475. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1483. ± 9.6kJ/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Deltar1446. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1454. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase

C6H5O2- + Hydrogen cation = Resorcinol

By formula: C6H5O2- + H+ = C6H6O2

Quantity Value Units Method Reference Comment
Deltar1450. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1444. ± 11.kJ/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Deltar1422. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1415. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase

C6H4FO- + Hydrogen cation = Phenol, 4-fluoro-

By formula: C6H4FO- + H+ = C6H5FO

Quantity Value Units Method Reference Comment
Deltar1451. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1455. ± 9.6kJ/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Deltar1422. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1426. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase

C7H4NO- + Hydrogen cation = Benzonitrile, 3-hydroxy-

By formula: C7H4NO- + H+ = C7H5NO

Quantity Value Units Method Reference Comment
Deltar1405. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1405. ± 9.6kJ/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Deltar1376. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1377. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase

C7H4NO- + Hydrogen cation = Benzonitrile, 4-hydroxy-

By formula: C7H4NO- + H+ = C7H5NO

Quantity Value Units Method Reference Comment
Deltar1390. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1392. ± 11.kJ/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Deltar1361. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1363. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase

C7H7O2- + Hydrogen cation = m-Guaiacol

By formula: C7H7O2- + H+ = C7H8O2

Quantity Value Units Method Reference Comment
Deltar1456. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1459. ± 9.6kJ/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Deltar1427. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1431. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase

C7H7O2- + Hydrogen cation = Mequinol

By formula: C7H7O2- + H+ = C7H8O2

Quantity Value Units Method Reference Comment
Deltar1466. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1469. ± 9.6kJ/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Deltar1437. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1440. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase

C6H4NO3- + Hydrogen cation = Phenol, 3-nitro-

By formula: C6H4NO3- + H+ = C6H5NO3

Quantity Value Units Method Reference Comment
Deltar1399. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1400. ± 11.kJ/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Deltar1370. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1371. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase

C7H7O- + Hydrogen cation = Phenol, 2-methyl-

By formula: C7H7O- + H+ = C7H8O

Quantity Value Units Method Reference Comment
Deltar1462. ± 9.2kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1465. ± 12.kJ/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Deltar1431. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1434. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase

C8H13O2- + Hydrogen cation = Cyclohexaneacetic acid

By formula: C8H13O2- + H+ = C8H14O2

Quantity Value Units Method Reference Comment
Deltar1445. ± 8.8kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Deltar1444. ± 8.8kJ/molG+TSJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1415. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase
Deltar1415. ± 8.4kJ/molIMREJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale

C2H3S- + Hydrogen cation = Thioacetaldehyde

By formula: C2H3S- + H+ = C2H4S

Quantity Value Units Method Reference Comment
Deltar1455. ± 14.kJ/molG+TSZhang and Grabowski, 1989gas phase; Between MeCO2H, EtCO2H (Acid = MeCH=S)
Deltar1461. ± 17.kJ/molG+TSGuillemin, Riague, et al., 2005gas phase; Acid: CH3CH=S
Quantity Value Units Method Reference Comment
Deltar1427. ± 13.kJ/molIMRBZhang and Grabowski, 1989gas phase; Between MeCO2H, EtCO2H (Acid = MeCH=S)
Deltar1432. ± 16.kJ/molIMRBGuillemin, Riague, et al., 2005gas phase; Acid: CH3CH=S

C11H15O2- + Hydrogen cation = Adamantane-1-carboxylic acid

By formula: C11H15O2- + H+ = C11H16O2

Quantity Value Units Method Reference Comment
Deltar1435. ± 8.8kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Deltar1438. ± 8.8kJ/molG+TSJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1406. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase
Deltar1408. ± 8.4kJ/molIMREJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale

C8H7O2- + Hydrogen cation = Benzeneacetic acid

By formula: C8H7O2- + H+ = C8H8O2

Quantity Value Units Method Reference Comment
Deltar1429. ± 8.8kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Deltar1427. ± 8.8kJ/molG+TSJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1400. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase
Deltar1398. ± 8.4kJ/molIMREJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale

C5H9O2- + Hydrogen cation = Propanoic acid, 2,2-dimethyl-

By formula: C5H9O2- + H+ = C5H10O2

Quantity Value Units Method Reference Comment
Deltar1442. ± 8.8kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Deltar1443. ± 8.8kJ/molG+TSJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1413. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase
Deltar1414. ± 8.4kJ/molIMREJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale

C4H3N2- + Hydrogen cation = Pyrazine

By formula: C4H3N2- + H+ = C4H4N2

Quantity Value Units Method Reference Comment
Deltar1643. ± 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.
Quantity Value Units Method Reference Comment
Deltar1604.6 ± 1.7kJ/molN/AWren, Vogelhuber, et al., 2012, 2gas phase
Deltar1603. ± 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.

Iodide + Hydrogen cation = Hydrogen iodide

By formula: I- + H+ = HI

Quantity Value Units Method Reference Comment
Deltar1315.24 ± 0.084kJ/molD-EAPelaez, Blondel, et al., 2009gas phase; Given: 3.0590463(38) eV
Deltar1312.1kJ/molN/ACheck, Faust, et al., 2001gas phase; Fe(CO)2-(q); ; «DELTA»S(EA)=5.0
Quantity Value Units Method Reference Comment
Deltar1294.03 ± 0.25kJ/molH-TSPelaez, Blondel, et al., 2009gas phase; Given: 3.0590463(38) eV
Deltar1290.8kJ/molN/ACheck, Faust, et al., 2001gas phase; Fe(CO)2-(q); ; «DELTA»S(EA)=5.0

C9H12BrO2- + Hydrogen cation = C9H13BrO2

By formula: C9H12BrO2- + H+ = C9H13BrO2

Quantity Value Units Method Reference Comment
Deltar1411. ± 9.2kJ/molG+TSKoppel, Mishima, et al., 1993gas phase
Deltar1411. ± 9.2kJ/molG+TSTaft and Topsom, 1987gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1382. ± 8.4kJ/molIMREKoppel, Mishima, et al., 1993gas phase
Deltar1382. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase; value altered from reference due to change in acidity scale

H5Si2- + Hydrogen cation = Disilane

By formula: H5Si2- + H+ = H6Si2

Quantity Value Units Method Reference Comment
Deltar<1312. ± 12.kJ/molAcidKrishnakumar and Srivastava, 1991gas phase; From Si2H6, AP = 0.0 eV/Data for SiH4 plus a-Si effects imply «DELTA»Hacid ca. 360. G3MP2B3 calculations give dHacid=360 kcal/mol
Quantity Value Units Method Reference Comment
Deltar<1275. ± 14.kJ/molH-TSKrishnakumar and Srivastava, 1991gas phase; From Si2H6, AP = 0.0 eV/Data for SiH4 plus a-Si effects imply «DELTA»Hacid ca. 360. G3MP2B3 calculations give dHacid=360 kcal/mol

C8H17O2- + Hydrogen cation = Heptanoic acid, 2-ethyl-

By formula: C8H17O2- + H+ = C9H18O2

Quantity Value Units Method Reference Comment
Deltar1416. ± 8.4kJ/molTDEqNorrman and McMahon, 1999gas phase; folded form. dSacid = 11.2 eu
Deltar1446. ± 8.4kJ/molTDEqNorrman and McMahon, 1999gas phase; Unfolded form
Quantity Value Units Method Reference Comment
Deltar1402. ± 8.8kJ/molH-TSNorrman and McMahon, 1999gas phase; folded form. dSacid = 11.2 eu
Deltar1412. ± 8.8kJ/molH-TSNorrman and McMahon, 1999gas phase; Unfolded form

C3H5O- + Hydrogen cation = Propanal

By formula: C3H5O- + H+ = C3H6O

Quantity Value Units Method Reference Comment
Deltar1528. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Deltar1531. ± 10.kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1501. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Deltar1504. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C9H9O- + Hydrogen cation = Benzyl methyl ketone

By formula: C9H9O- + H+ = C9H10O

Quantity Value Units Method Reference Comment
Deltar1465. ± 10.kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Deltar1469. ± 15.kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1441. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Deltar1445. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C5H4F3O2- + Hydrogen cation = 2,4-Pentanedione, 1,1,1-trifluoro-

By formula: C5H4F3O2- + H+ = C5H5F3O2

Quantity Value Units Method Reference Comment
Deltar1374. ± 12.kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1374. ± 17.kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1347. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1348. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C8H6N- + Hydrogen cation = Benzyl nitrile

By formula: C8H6N- + H+ = C8H7N

Quantity Value Units Method Reference Comment
Deltar1467. ± 9.6kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1471. ± 13.kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1440. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Deltar1443. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C13H11- + Hydrogen cation = Diphenylmethane

By formula: C13H11- + H+ = C13H12

Quantity Value Units Method Reference Comment
Deltar1521. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Deltar1512. ± 9.6kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1499. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Deltar1489. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C4H6ClO2- + Hydrogen cation = Butanoic acid, 2-chloro-

By formula: C4H6ClO2- + H+ = C4H7ClO2

Quantity Value Units Method Reference Comment
Deltar1410. ± 8.8kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase; dHf(AH) from GpAd in Stein, Rikkers, et al. is seriously in error
Deltar1412. ± 9.6kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1383. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase; dHf(AH) from GpAd in Stein, Rikkers, et al. is seriously in error
Deltar1384. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C9H9O- + Hydrogen cation = 1-Propanone, 1-phenyl-

By formula: C9H9O- + H+ = C9H10O

Quantity Value Units Method Reference Comment
Deltar1508. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Deltar1509. ± 21.kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1481. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Deltar1482. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C2H4NO2- + Hydrogen cation = Ethane, nitro-

By formula: C2H4NO2- + H+ = C2H5NO2

Quantity Value Units Method Reference Comment
Deltar1489. ± 9.2kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Deltar1496. ± 12.kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1462. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Deltar1469. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C3H6NO2- + Hydrogen cation = Propane, 2-nitro-

By formula: C3H6NO2- + H+ = C3H7NO2

Quantity Value Units Method Reference Comment
Deltar1490. ± 9.2kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Deltar1491. ± 12.kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1464. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Deltar1466. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C2H5OS- + Hydrogen cation = Dimethyl Sulfoxide

By formula: C2H5OS- + H+ = C2H6OS

Quantity Value Units Method Reference Comment
Deltar1563. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Deltar1566. ± 9.6kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1533. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Deltar1536. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C2H5O2S- + Hydrogen cation = Dimethyl sulfone

By formula: C2H5O2S- + H+ = C2H6O2S

Quantity Value Units Method Reference Comment
Deltar1531. ± 9.2kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Deltar1533. ± 12.kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1499. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Deltar1502. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C3H4ClO2- + Hydrogen cation = Propanoic acid, 2-chloro-

By formula: C3H4ClO2- + H+ = C3H5ClO2

Quantity Value Units Method Reference Comment
Deltar1410. ± 8.8kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase; dHf(AH) from GpAd in Stein, Rikkers, et al. is seriously in error
Deltar1407. ± 9.6kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1382. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase; dHf(AH) from GpAd in Stein, Rikkers, et al. is seriously in error
Deltar1380. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C10H19O2- + Hydrogen cation = n-Decanoic acid

By formula: C10H19O2- + H+ = C10H20O2

Quantity Value Units Method Reference Comment
Deltar1418. ± 8.4kJ/molTDEqNorrman and McMahon, 1999gas phase; Folded form; dSacid = 7.2 eu
Deltar1448. ± 8.4kJ/molTDEqNorrman and McMahon, 1999gas phase; Unfolded form
Quantity Value Units Method Reference Comment
Deltar1409. ± 8.8kJ/molH-TSNorrman and McMahon, 1999gas phase; Folded form; dSacid = 7.2 eu
Deltar1418. ± 8.8kJ/molH-TSNorrman and McMahon, 1999gas phase; Unfolded form

C7H4F3- + Hydrogen cation = Benzene, (trifluoromethyl)-

By formula: C7H4F3- + H+ = C7H5F3

Quantity Value Units Method Reference Comment
Deltar1620. ± 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.
Quantity Value Units Method Reference Comment
Deltar1584. ± 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.
Deltar1586. ± 21.kJ/molIMRBBartmess and McIver Jr., 1979gas phase

C3H6N- + Hydrogen cation = C3H7N

By formula: C3H6N- + H+ = C3H7N

Quantity Value Units Method Reference Comment
Deltar1593. ± 18.kJ/molG+TSDahlke and Kass, 1991gas phase; From CH2=CHCH2NH2 + HO-. Between MeOH, EtOH in acidity. Reprotonation structure uncertain.Acid take as EtCH=NH for this acidity.
Quantity Value Units Method Reference Comment
Deltar1559. ± 17.kJ/molIMRBDahlke and Kass, 1991gas phase; From CH2=CHCH2NH2 + HO-. Between MeOH, EtOH in acidity. Reprotonation structure uncertain.Acid take as EtCH=NH for this acidity.

C3H9OSi- + Hydrogen cation = Silanol, trimethyl-

By formula: C3H9OSi- + H+ = C3H10OSi

Quantity Value Units Method Reference Comment
Deltar1518. ± 19.kJ/molG+TSAngelini, Johnson, et al., 1991gas phase; Between CF2HCH2OH, CF3CH2OH
Deltar1502. ± 17.kJ/molG+TSDamrauer, Simon, et al., 1991gas phase; between pyrrole, CF3CH2OH
Quantity Value Units Method Reference Comment
Deltar1492. ± 19.kJ/molIMRBAngelini, Johnson, et al., 1991gas phase; Between CF2HCH2OH, CF3CH2OH
Deltar1475. ± 17.kJ/molIMRBDamrauer, Simon, et al., 1991gas phase; between pyrrole, CF3CH2OH

C3H2N- + Hydrogen cation = 2-Propenenitrile

By formula: C3H2N- + H+ = C3H3N

Quantity Value Units Method Reference Comment
Deltar1553. ± 9.2kJ/molG+TSBartmess, 1980gas phase; value altered from reference due to change in acidity scale
Deltar1524. ± 19.kJ/molEIAEHeni and Illenberger, 1986gas phase; From CH2=CHCN. G3MP2B3 calculations indicate a dHacdi ca. 374 kcal/mol
Quantity Value Units Method Reference Comment
Deltar1528. ± 8.4kJ/molIMREBartmess, 1980gas phase; value altered from reference due to change in acidity scale

C7H4NO4- + Hydrogen cation = Benzoic acid, 3-nitro-

By formula: C7H4NO4- + H+ = C7H5NO4

Quantity Value Units Method Reference Comment
Deltar1377. ± 8.8kJ/molG+TSTaft, 1987gas phase; value altered from reference due to change in acidity scale
Deltar1377. ± 8.8kJ/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Deltar1347. ± 8.4kJ/molIMRETaft, 1987gas phase; value altered from reference due to change in acidity scale
Deltar1348. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase

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.

Römer, Janaway, et al., 1997
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Taft and Bordwell, 1988
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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]

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]

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]

Pariat and Allan, 1991
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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]

Wetzel and Brauman, 1988
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DePuy and Damrauer, 1984
DePuy, C.H.; Damrauer, R., Reactions of organosilane anionic species with nitrous oxide, Organometallics, 1984, 3, 362. [all data]

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Schwartz, R.L.; Davico, G.E.; Lineberger, W.C., Negative-ion photoelectron spectroscopy of CH3S-, J. Electron Spectros. Rel. Phenom., 2000, 108, 1-3, 163-168, https://doi.org/10.1016/S0368-2048(00)00125-0 . [all data]

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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]

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Gianola, A.J.; Ichino, T.; Kato, S.; Bierbaum, V.M.; Lineberger, W.C., Thermochemical studies of pyrazolide, J. Phys. Chem. A, 2006, 110, 27, 8457-8466, https://doi.org/10.1021/jp057499+ . [all data]

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Fujio, McIver, et al., 1981
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Kebarle and McMahon, 1977
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Jinfeng, C.; Topsom, R.D.; Headley, A.D.; Koppel, I.; Mishima, M.; Taft, R.W.; Veji, S., Acidities of Substituted Acetic Acids, J. Mol. Struct., 1988, 168, 141, https://doi.org/10.1016/0166-1280(88)80349-X . [all data]

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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]

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Krishnakumar, E.; Srivastava, S.K., Dissociative Electron Attachment of Electrons with Si2H6, Int. J. Mass Spectrom. Ion Proc., 1991, 103, 2-3, 107, https://doi.org/10.1016/0168-1176(91)80082-X . [all data]

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Bartmess, J.E.; McIver Jr., The Gas Phase Acidity Scale in Gas Phase Ion Chemistry, Gas Phase Ion Chemistry, V. 2, M.T. Bowers, Ed., Academic Press, NY, 1979, Ch. 11, Elsevier, 1979. [all data]

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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]

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Heni and Illenberger, 1986
Heni, M.; Illenberger, E., Electron attachment by saturated nitriles. Acrylonitrile (CH2H3CN), and benzonitrile (C6H5CN), Int. J. Mass Spectrom. Ion Phys., 1986, 73, 127. [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]


Notes

Go To: Top, Reaction thermochemistry data, References