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Hydrogen cation


Reaction thermochemistry data

Go To: Top, References, Notes

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 1151 to 1200

C16F14N- + Hydrogen cation = C16HF14N

By formula: C16F14N- + H+ = C16HF14N

Quantity Value Units Method Reference Comment
Deltar1264. ± 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.

C19F13- + Hydrogen cation = C19HF13

By formula: C19F13- + H+ = C19HF13

Quantity Value Units Method Reference Comment
Deltar1263. ± 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.

C13F7N2- + Hydrogen cation = C13HF7N2

By formula: C13F7N2- + H+ = C13HF7N2

Quantity Value Units Method Reference Comment
Deltar1263. ± 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.

C10F7N2- + Hydrogen cation = C10HF7N2

By formula: C10F7N2- + H+ = C10HF7N2

Quantity Value Units Method Reference Comment
Deltar1261. ± 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.

C4H9S- + Hydrogen cation = 1-Butanethiol

By formula: C4H9S- + H+ = C4H10S

Quantity Value Units Method Reference Comment
Deltar1480. ± 9.2kJ/molG+TSTaft and Bordwell, 1988gas phase
Quantity Value Units Method Reference Comment
Deltar1454. ± 8.4kJ/molIMRETaft and Bordwell, 1988gas phase

C9H8NO- + Hydrogen cation = (3-Methoxyphenyl)acetonitrile

By formula: C9H8NO- + H+ = C9NO

Quantity Value Units Method Reference Comment
Deltar1461. ± 10.kJ/molG+TSTaft and Topsom, 1987gas phase
Quantity Value Units Method Reference Comment
Deltar1434. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase

C9H8N- + Hydrogen cation = 3-Methylbenzyl cyanide

By formula: C9H8N- + H+ = C9H9N

Quantity Value Units Method Reference Comment
Deltar1468. ± 10.kJ/molG+TSTaft and Topsom, 1987gas phase
Quantity Value Units Method Reference Comment
Deltar1440. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase

C9F5N2- + Hydrogen cation = C9HF5N2

By formula: C9F5N2- + H+ = C9HF5N2

Quantity Value Units Method Reference Comment
Deltar1270. ± 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.

C7H8NO2S- + Hydrogen cation = C7H9NO2S

By formula: C7H8NO2S- + H+ = C7H9NO2S

Quantity Value Units Method Reference Comment
Deltar1475. ± 8.8kJ/molG+TSTaft and Topsom, 1987gas phase
Quantity Value Units Method Reference Comment
Deltar1445. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase

C9H9O2S- + Hydrogen cation = C9H10O2S

By formula: C9H9O2S- + H+ = C9H10O2S

Quantity Value Units Method Reference Comment
Deltar1512. ± 9.6kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1485. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C9H11O2S- + Hydrogen cation = Benzene, (propylsulfonyl)-

By formula: C9H11O2S- + H+ = C9H12O2S

Quantity Value Units Method Reference Comment
Deltar1523. ± 8.4kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1491. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C10H13O2S- + Hydrogen cation = C10H14O2S

By formula: C10H13O2S- + H+ = C10H14O2S

Quantity Value Units Method Reference Comment
Deltar1517. ± 9.6kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1487. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C9H12N- + Hydrogen cation = Benzenamine, N,N,3-trimethyl-

By formula: C9H12N- + H+ = C9H13N

Quantity Value Units Method Reference Comment
Deltar1597. ± 21.kJ/molG+TSCaldwell and Bartmessgas phase
Quantity Value Units Method Reference Comment
Deltar1569. ± 21.kJ/molIMRBCaldwell and Bartmessgas phase

C9H5F6- + Hydrogen cation = C9H6F6

By formula: C9H5F6- + H+ = C9H6F6

Quantity Value Units Method Reference Comment
Deltar1510. ± 8.8kJ/molG+TSTaft and Topsom, 1987gas phase
Quantity Value Units Method Reference Comment
Deltar1482. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase

C5H7O3- + Hydrogen cation = 2-Propanone, 1-(acetyloxy)-

By formula: C5H7O3- + H+ = C5H8O3

Quantity Value Units Method Reference Comment
Deltar1466. ± 12.kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1436. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C7H4F3OS- + Hydrogen cation = C7H5F3OS

By formula: C7H4F3OS- + H+ = C7H5F3OS

Quantity Value Units Method Reference Comment
Deltar1411. ± 8.8kJ/molG+TSTaft and Topsom, 1987gas phase
Quantity Value Units Method Reference Comment
Deltar1382. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase

C7H4F3O3S- + Hydrogen cation = C7H5F3O3S

By formula: C7H4F3O3S- + H+ = C7H5F3O3S

Quantity Value Units Method Reference Comment
Deltar1379. ± 8.8kJ/molG+TSTaft and Topsom, 1987gas phase
Quantity Value Units Method Reference Comment
Deltar1350. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase

C7H5N2- + Hydrogen cation = Benzonitrile, m-amino-

By formula: C7H5N2- + H+ = C7H6N2

Quantity Value Units Method Reference Comment
Deltar1477. ± 8.8kJ/molG+TSTaft and Topsom, 1987gas phase
Quantity Value Units Method Reference Comment
Deltar1446. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase

C8H8NO2- + Hydrogen cation = Benzoic acid, 3-amino-, methyl ester

By formula: C8H8NO2- + H+ = C8NO2

Quantity Value Units Method Reference Comment
Deltar1509. ± 8.8kJ/molG+TSTaft and Topsom, 1987gas phase
Quantity Value Units Method Reference Comment
Deltar1478. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase

C9H5F3N- + Hydrogen cation = Benzeneacetonitrile, 3-(trifluoromethyl)-

By formula: C9H5F3N- + H+ = C9H6F3N

Quantity Value Units Method Reference Comment
Deltar1431. ± 10.kJ/molG+TSTaft and Topsom, 1987gas phase
Quantity Value Units Method Reference Comment
Deltar1403. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase

C9H5F3N- + Hydrogen cation = 4-(Trifluoromethyl)phenylacetonitrile

By formula: C9H5F3N- + H+ = C9H6F3N

Quantity Value Units Method Reference Comment
Deltar1420. ± 10.kJ/molG+TSTaft and Topsom, 1987gas phase
Quantity Value Units Method Reference Comment
Deltar1393. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase

C7H7O2S- + Hydrogen cation = Sulfone, methyl phenyl

By formula: C7H7O2S- + H+ = C7H8O2S

Quantity Value Units Method Reference Comment
Deltar1518. ± 9.6kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1487. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C9H12N- + Hydrogen cation = Benzenamine, N,N,4-trimethyl-

By formula: C9H12N- + H+ = C9H13N

Quantity Value Units Method Reference Comment
Deltar1614. ± 21.kJ/molG+TSCaldwell and Bartmessgas phase
Quantity Value Units Method Reference Comment
Deltar1586. ± 21.kJ/molIMRBCaldwell and Bartmessgas phase

C8H6F3O2S- + Hydrogen cation = C8H7F3O2S

By formula: C8H6F3O2S- + H+ = C8H7F3O2S

Quantity Value Units Method Reference Comment
Deltar1251. ± 8.4kJ/molIMRETaft, 1991gas phase; Probably wrong: in Koppel, Taft, et al., 1994, (CF3SO2)2CHPh is 301; CF3SO2NHPh is 313.5

C6H19Si3- + Hydrogen cation = C6H20Si3

By formula: C6H19Si3- + H+ = C6H20Si3

Quantity Value Units Method Reference Comment
Deltar1477. ± 18.kJ/molD-EABrinkman, Berger, et al., 1994gas phase; BDE revised, based on data for DH of (Me3Si)3Si-H in Laarhoven, Mulder, et al., 1999

C8H3F6O- + Hydrogen cation = 3,5-Bis(trifluoromethyl)phenol

By formula: C8H3F6O- + H+ = C8H4F6O

Quantity Value Units Method Reference Comment
Deltar1379. ± 8.8kJ/molG+TSTaft and Topsom, 1987gas phase
Quantity Value Units Method Reference Comment
Deltar1351. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase

C3H2NO2- + Hydrogen cation = Acetic acid, cyano-

By formula: C3H2NO2- + H+ = C3H3NO2

Quantity Value Units Method Reference Comment
Deltar1382. ± 8.8kJ/molG+TSTaft and Topsom, 1987gas phase
Quantity Value Units Method Reference Comment
Deltar1354. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase

C7H5F3NS- + Hydrogen cation = C7H6F3NS

By formula: C7H5F3NS- + H+ = C7H6F3NS

Quantity Value Units Method Reference Comment
Deltar1487. ± 8.8kJ/molG+TSTaft and Topsom, 1987gas phase
Quantity Value Units Method Reference Comment
Deltar1456. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase

C7H5F3NO2S- + Hydrogen cation = C7H6F3NO2S

By formula: C7H5F3NO2S- + H+ = C7H6F3NO2S

Quantity Value Units Method Reference Comment
Deltar1451. ± 8.8kJ/molG+TSTaft and Topsom, 1987gas phase
Quantity Value Units Method Reference Comment
Deltar1421. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase

C8H4F6N- + Hydrogen cation = Benzenamine, 3,5-bis(trifluoromethyl)-

By formula: C8H4F6N- + H+ = C8H5F6N

Quantity Value Units Method Reference Comment
Deltar1456. ± 8.8kJ/molG+TSTaft and Topsom, 1987gas phase
Quantity Value Units Method Reference Comment
Deltar1425. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase

C4H6NO2- + Hydrogen cation = Diacetamide

By formula: C4H6NO2- + H+ = C4H7NO2

Quantity Value Units Method Reference Comment
Deltar1451. ± 15.kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1422. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C8H5N2O2- + Hydrogen cation = Benzeneacetonitrile, 3-nitro-

By formula: C8H5N2O2- + H+ = C8H6N2O2

Quantity Value Units Method Reference Comment
Deltar1412. ± 10.kJ/molG+TSTaft and Topsom, 1987gas phase
Quantity Value Units Method Reference Comment
Deltar1384. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase

C8H9O2S- + Hydrogen cation = Benzene, (ethylsulfonyl)-

By formula: C8H9O2S- + H+ = C8H10O2S

Quantity Value Units Method Reference Comment
Deltar1527. ± 8.4kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1495. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C7H6NO- + Hydrogen cation = m-nitrosotoluene

By formula: C7H6NO- + H+ = C7H7NO

Quantity Value Units Method Reference Comment
Deltar1539. ± 8.8kJ/molG+TSTaft and Topsom, 1987gas phase
Quantity Value Units Method Reference Comment
Deltar1511. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase

C4H6NO- + Hydrogen cation = Propanenitrile, 3-methoxy-

By formula: C4H6NO- + H+ = C4H7N

Quantity Value Units Method Reference Comment
Deltar1568. ± 8.8kJ/molG+TSBartmess, 1980gas phase
Quantity Value Units Method Reference Comment
Deltar1536. ± 8.4kJ/molIMREBartmess, 1980gas phase

C6H5N2O2- + Hydrogen cation = m-Nitroaniline

By formula: C6H5N2O2- + H+ = C6H6N2O2

Quantity Value Units Method Reference Comment
Deltar1474. ± 8.8kJ/molG+TSTaft and Topsom, 1987gas phase
Quantity Value Units Method Reference Comment
Deltar1443. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase

C4H7O- + Hydrogen cation = 2-Butanone

By formula: C4H7O- + H+ = C4H8O

Quantity Value Units Method Reference Comment
Deltar1540. ± 12.kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1512. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C10H9O2- + Hydrogen cation = 1,3-Butanedione, 1-phenyl-

By formula: C10H9O2- + H+ = C10H10O2

Quantity Value Units Method Reference Comment
Deltar1422. ± 9.6kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1393. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

L-Aspartamide anion + Hydrogen cation = Isoglutamine

By formula: C4H7N2O3- + H+ = C5H10N2O3

Quantity Value Units Method Reference Comment
Deltar1366. ± 15.kJ/molIMRBLi, Matus, et al., 2007gas phase; Calculations indicate cyclized (H-bonded) anion; side chain acidic site

C5H9N2O3- + Hydrogen cation = C5H10N2O3

By formula: C5H9N2O3- + H+ = C5H10N2O3

Quantity Value Units Method Reference Comment
Deltar1375. ± 20.kJ/molIMRBLi, Matus, et al., 2007gas phase; Calculations indicate cyclized (H-bonded) anion; side chain acidic site

C6H4NO2- + Hydrogen cation = C6H5NO2

By formula: C6H4NO2- + H+ = C6H5NO2

Quantity Value Units Method Reference Comment
Deltar1406. ± 13.kJ/molCIDCMichelson, Petronico, et al., 2012gas phase; Calcs: enol and keto forms of the acid are comparable in stability

C14H11O- + Hydrogen cation = 9-Methoxyfluorene

By formula: C14H11O- + H+ = C14H12O

Quantity Value Units Method Reference Comment
Deltar1469. ± 8.8kJ/molG+TSTaft, 1991gas phase
Quantity Value Units Method Reference Comment
Deltar1436. ± 8.4kJ/molIMRETaft, 1991gas phase

C5H4F3N2- + Hydrogen cation = 1H-Pyrazole, 3-methyl-5-(trifluoromethyl)-

By formula: C5H4F3N2- + H+ = C5H5F3N2

Quantity Value Units Method Reference Comment
Deltar1428. ± 8.8kJ/molG+TSTaft, 1991gas phase
Quantity Value Units Method Reference Comment
Deltar1396. ± 8.4kJ/molIMRETaft, 1991gas phase

C4H5N2- + Hydrogen cation = 1H-Pyrazole, 3-methyl-

By formula: C4H5N2- + H+ = C4H6N2

Quantity Value Units Method Reference Comment
Deltar1490. ± 8.8kJ/molG+TSTaft, 1991gas phase
Quantity Value Units Method Reference Comment
Deltar1457. ± 8.4kJ/molIMRETaft, 1991gas phase

C6H9N2- + Hydrogen cation = 3,4,5-Trimethylpyrazole

By formula: C6H9N2- + H+ = C6H10N2

Quantity Value Units Method Reference Comment
Deltar1492. ± 8.8kJ/molG+TSTaft, 1991gas phase
Quantity Value Units Method Reference Comment
Deltar1461. ± 8.4kJ/molIMRETaft, 1991gas phase

C5H7N2- + Hydrogen cation = 1H-Pyrazole, 3,4-dimethyl-

By formula: C5H7N2- + H+ = C5H8N2

Quantity Value Units Method Reference Comment
Deltar1488. ± 8.8kJ/molG+TSTaft, 1991gas phase
Quantity Value Units Method Reference Comment
Deltar1456. ± 8.4kJ/molIMRETaft, 1991gas phase

C8H12B- + Hydrogen cation = C8H13B

By formula: C8H12B- + H+ = C8H13B

Quantity Value Units Method Reference Comment
Deltar1544. ± 17.kJ/molG+TSSullivan, 1977gas phase
Quantity Value Units Method Reference Comment
Deltar1515. ± 17.kJ/molIMRBSullivan, 1977gas phase

C8H8NO- + Hydrogen cation = Benzeneacetamide

By formula: C8H8NO- + H+ = C8H9NO

Quantity Value Units Method Reference Comment
Deltar1479. ± 9.2kJ/molG+TSTaft, 1991gas phase
Quantity Value Units Method Reference Comment
Deltar1455. ± 8.4kJ/molIMRETaft, 1991gas phase

C9H7O- + Hydrogen cation = 2H-Inden-2-one, 1,3-dihydro-

By formula: C9H7O- + H+ = C9H8O

Quantity Value Units Method Reference Comment
Deltar1469. ± 8.8kJ/molG+TSTaft, 1991gas phase
Quantity Value Units Method Reference Comment
Deltar1437. ± 8.4kJ/molIMRETaft, 1991gas phase

C2H2N3- + Hydrogen cation = 1H-1,2,4-Triazole

By formula: C2H2N3- + H+ = C2H3N3

Quantity Value Units Method Reference Comment
Deltar1440. ± 8.8kJ/molG+TSTaft, 1991gas phase
Quantity Value Units Method Reference Comment
Deltar1410. ± 8.4kJ/molIMRETaft, 1991gas 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.

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]

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]

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]

Caldwell and Bartmess
Caldwell, G.; Bartmess, J.E., , Unpublished results. [all data]

Taft, 1991
Taft, R.W., , personal communication, Aug, 1991. [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]

Laarhoven, Mulder, et al., 1999
Laarhoven, L.J.J.; Mulder, P.; Wayner, D.D.M., Determination of bond dissociation enthalpies in solution by photoacoustic calorimetry, Acc. Chem. Res., 1999, 32, 4, 342-349, https://doi.org/10.1021/ar9703443 . [all data]

Bartmess, 1980
Bartmess, J.E., Solvent effects on ion-molecule reactions. Vinyl anions vs. conjugate addition, J. Am. Chem. Soc., 1980, 102, 2483. [all data]

Li, Matus, et al., 2007
Li, Z.; Matus, M.H.; Velazquez, H.A.; Dixon, D.A.; Cassady, C.J., Gas-phase acidities of aspartic acid, glutamic acid, and their amino acid amides, Int. J. Mass Spectrom., 2007, 265, 2-3, 213-223, https://doi.org/10.1016/j.ijms.2007.02.009 . [all data]

Michelson, Petronico, et al., 2012
Michelson, A.Z.; Petronico, A.; Lee, J.K., 2-Pyridone and Derivatives: Gas-Phase Acidity, Proton Affinity, Tautomer Preference, and Leaving Group Ability, J. Org. Chem., 2012, 77, 4, 1623-1631, https://doi.org/10.1021/jo201991y . [all data]

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


Notes

Go To: Top, Reaction thermochemistry data, References