Home Symbol which looks like a small house Up Solid circle with an upward pointer in it

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 351 to 400

C3H4BrO2- + Hydrogen cation = 2-Bromopropanoic acid

By formula: C3H4BrO2- + H+ = C3H5BrO2

Quantity Value Units Method Reference Comment
Deltar1409. ± 8.8kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Deltar1407. ± 8.8kJ/molG+TSCaldwell, McMahon, et al., 1985gas phase
Quantity Value Units Method Reference Comment
Deltar1380. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase
Deltar1377. ± 8.4kJ/molIMRECaldwell, McMahon, et al., 1985gas phase

Si- + Hydrogen cation = Silylidyne

By formula: Si- + H+ = HSi

Quantity Value Units Method Reference Comment
Deltar1477. ± 11.kJ/molD-EABlondel, Chaibi, et al., 2005gas phase; (28)Si: 1.3895213(13) eV; revised analysis of Blondel, Delsart, et al., 2001
Quantity Value Units Method Reference Comment
Deltar1456. ± 12.kJ/molH-TSBlondel, Chaibi, et al., 2005gas phase; (28)Si: 1.3895213(13) eV; revised analysis of Blondel, Delsart, et al., 2001

C4H6BrO2- + Hydrogen cation = 2-Bromobutyric acid

By formula: C4H6BrO2- + H+ = C4H7BrO2

Quantity Value Units Method Reference Comment
Deltar1409. ± 8.8kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Deltar1407. ± 8.8kJ/molG+TSCaldwell, McMahon, et al., 1985gas phase
Quantity Value Units Method Reference Comment
Deltar1380. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase
Deltar1378. ± 8.4kJ/molIMRECaldwell, McMahon, et al., 1985gas phase

C6H11O2- + Hydrogen cation = Butanoic acid, 3,3-dimethyl-

By formula: C6H11O2- + H+ = C6H12O2

Quantity Value Units Method Reference Comment
Deltar1443. ± 8.8kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Deltar1444. ± 8.8kJ/molG+TSTaft and Topsom, 1987gas phase
Quantity Value Units Method Reference Comment
Deltar1413. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase
Deltar1415. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase

C3H2F3O2- + Hydrogen cation = Propanoic acid, 3,3,3-trifluoro-

By formula: C3H2F3O2- + H+ = C3H3F3O2

Quantity Value Units Method Reference Comment
Deltar1397. ± 8.8kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Deltar1400. ± 8.8kJ/molG+TSTaft and Topsom, 1987gas phase
Quantity Value Units Method Reference Comment
Deltar1368. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase
Deltar1371. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase

C6H13Si- + Hydrogen cation = Silane, trimethyl-2-propenyl-

By formula: C6H13Si- + H+ = C6H14Si

Quantity Value Units Method Reference Comment
Deltar<1592.3 ± 3.8kJ/molG+TSDePuy, Bierbaum, et al., 1980gas phase; More acidic than MeOH. Computations indicate dGacid ca. 367 kcal/mol
Quantity Value Units Method Reference Comment
Deltar<1564.8kJ/molIMRBDePuy, Bierbaum, et al., 1980gas phase; More acidic than MeOH. Computations indicate dGacid ca. 367 kcal/mol

C5H9O2- + Hydrogen cation = Butanoic acid, 3-methyl-

By formula: C5H9O2- + H+ = C5H10O2

Quantity Value Units Method Reference Comment
Deltar1446. ± 8.8kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Deltar1451. ± 8.8kJ/molG+TSTaft and Topsom, 1987gas phase
Quantity Value Units Method Reference Comment
Deltar1416. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase
Deltar1421. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase

C4H2NO2- + Hydrogen cation = 1H-Pyrrole-2,5-dione

By formula: C4H2NO2- + H+ = C4H3NO2

Quantity Value Units Method Reference Comment
Deltar1360. ± 19.kJ/molEIAECooper and Compton, 1973gas phase; From maleimide. G3MP2B3 calculations indicate a dHacid = 342 kcal/mol
Quantity Value Units Method Reference Comment
Deltar1328. ± 21.kJ/molH-TSCooper and Compton, 1973gas phase; From maleimide. G3MP2B3 calculations indicate a dHacid = 342 kcal/mol

C4H6ClO2- + Hydrogen cation = Butanoic acid, 3-chloro-

By formula: C4H6ClO2- + H+ = C4H7ClO2

Quantity Value Units Method Reference Comment
Deltar1430. ± 11.kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Deltar1431. ± 16.kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1401. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase
Deltar1401. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

EtCO2 anion + Hydrogen cation = Propanoic acid

By formula: C3H5O2- + H+ = C3H6O2

Quantity Value Units Method Reference Comment
Deltar1454. ± 9.2kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Deltar1454. ± 12.kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1424. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase
Deltar1424. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C3H4ClO2- + Hydrogen cation = Propanoic acid, 3-chloro-

By formula: C3H4ClO2- + H+ = C3H5ClO2

Quantity Value Units Method Reference Comment
Deltar1426. ± 11.kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Deltar1426. ± 16.kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1397. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase
Deltar1397. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C4H6ClO2- + Hydrogen cation = Butanoic acid, 4-chloro-

By formula: C4H6ClO2- + H+ = C4H7ClO2

Quantity Value Units Method Reference Comment
Deltar1446. ± 11.kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Deltar1445. ± 16.kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1417. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase
Deltar1416. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C8H8NO- + Hydrogen cation = Acetamide, N-phenyl-

By formula: C8H8NO- + H+ = C8H9NO

Quantity Value Units Method Reference Comment
Deltar1454. ± 8.8kJ/molG+TSTaft and Bordwell, 1988gas phase
Deltar1476. ± 9.6kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1425. ± 8.4kJ/molIMRETaft and Bordwell, 1988gas phase
Deltar1447. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

dihydropentalenide anion + Hydrogen cation = 1,5-Dihydropentalene

By formula: C8H7- + H+ = C8H8

Quantity Value Units Method Reference Comment
Deltar1484. ± 18.kJ/molG+TSKato, Gareyev, et al., 1998gas phase; Acid: bicyclo[3.3.0]octa-1(5),2,6-triene. Between MeSH, tBuSH.
Quantity Value Units Method Reference Comment
Deltar1458. ± 18.kJ/molIMRBKato, Gareyev, et al., 1998gas phase; Acid: bicyclo[3.3.0]octa-1(5),2,6-triene. Between MeSH, tBuSH.

C2H2BrO2- + Hydrogen cation = Acetic acid, bromo-

By formula: C2H2BrO2- + H+ = C2H3BrO2

Quantity Value Units Method Reference Comment
Deltar1401. ± 9.6kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase
Deltar1397. ± 13.kJ/molG+TSCumming and Kebarle, 1978gas phase
Quantity Value Units Method Reference Comment
Deltar1373. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase
Deltar1370. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase

C5H7- + Hydrogen cation = Bicyclo[1.1.1]pentane

By formula: C5H7- + H+ = C5H8

Quantity Value Units Method Reference Comment
Deltar1720. ± 15.kJ/molCIDTGraul and Squires, 1990gas phase; Reed, Kass, et al., 2002 claim this is the 1,4-pentadien-2-ide anion
Quantity Value Units Method Reference Comment
Deltar1684. ± 15.kJ/molH-TSGraul and Squires, 1990gas phase; Reed, Kass, et al., 2002 claim this is the 1,4-pentadien-2-ide anion

C10H7N2- + Hydrogen cation = C10H8N2

By formula: C10H7N2- + H+ = C10H8N2

Quantity Value Units Method Reference Comment
Deltar1351. ± 9.2kJ/molG+TSKoppel, Taft, et al., 1994gas phase
Quantity Value Units Method Reference Comment
Deltar1321. ± 8.4kJ/molIMREKoppel, Taft, et al., 1994gas phase
Deltar1323. ± 8.4kJ/molIMREJinfeng, Topsom, et al., 1988gas phase; value altered from reference due to change in acidity scale

MeCH(OH)CO2 anion + Hydrogen cation = dl-lactic acid

By formula: C3H5O3- + H+ = C3H6O3

Quantity Value Units Method Reference Comment
Deltar1413. ± 9.2kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase; May have large entropy correction from cyclization; see HOCH2CO2-
Quantity Value Units Method Reference Comment
Deltar1383. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase; May have large entropy correction from cyclization; see HOCH2CO2-

Cl3Si- + Hydrogen cation = Trichlorosilane

By formula: Cl3Si- + H+ = HCl3Si

Quantity Value Units Method Reference Comment
Deltar<1510. ± 10.kJ/molD-EAPabst, Margrave, et al., 1977gas phase; From SiCl4. G3MP2B3 calculations indicate an EA of ca. 3.0 eV.
Quantity Value Units Method Reference Comment
Deltar<1478. ± 10.kJ/molH-TSPabst, Margrave, et al., 1977gas phase; From SiCl4. G3MP2B3 calculations indicate an EA of ca. 3.0 eV.

C10H10NO2- + Hydrogen cation = C10H11NO2

By formula: C10H10NO2- + H+ = C10H11NO2

Quantity Value Units Method Reference Comment
Deltar1395. ± 9.2kJ/molG+TSKoppel, Mishima, et al., 1993gas phase
Quantity Value Units Method Reference Comment
Deltar1365. ± 8.4kJ/molIMREKoppel, Mishima, et al., 1993gas phase
Deltar1365. ± 8.4kJ/molIMRETaft and Topsom, 1987gas phase; value altered from reference due to change in acidity scale

C3F8NO4S2- + Hydrogen cation = C3HF8NO4S2

By formula: C3F8NO4S2- + H+ = C3HF8NO4S2

Quantity Value Units Method Reference Comment
Deltar1193. ± 8.4kJ/molIMRELeito, Raamat, et al., 2009gas phase
Deltar1215. ± 8.4kJ/molIMREKoppel, Taft, et al., 1994gas phase; Per Leito, Raamat, et al., 2009, dGacid is likely too weak by at least 5.3 kcal/mol, due to problems in the ladder at dGacid=293 and 299.

C4F10NO4S2- + Hydrogen cation = C4HF10NO4S2

By formula: C4F10NO4S2- + H+ = C4HF10NO4S2

Quantity Value Units Method Reference Comment
Deltar1187. ± 8.4kJ/molIMRELeito, Raamat, et al., 2009gas phase
Deltar1211. ± 8.4kJ/molIMREKoppel, Taft, et al., 1994gas phase; Per Leito, Raamat, et al., 2009, dGacid is likely too weak by at least 5.3 kcal/mol, due to problems in the ladder at dGacid=293 and 299.

C3F6NO4S2- + Hydrogen cation = C3HF6NO4S2

By formula: C3F6NO4S2- + H+ = C3HF6NO4S2

Quantity Value Units Method Reference Comment
Deltar1189. ± 8.4kJ/molIMRELeito, Raamat, et al., 2009gas phase
Deltar1212. ± 8.4kJ/molIMREKoppel, Taft, et al., 1994gas phase; Per Leito, Raamat, et al., 2009, dGacid is likely too weak by at least 5.3 kcal/mol, due to problems in the ladder at dGacid=293 and 299.

C7H5O- + Hydrogen cation = C7H6O

By formula: C7H5O- + H+ = C7H6O

Quantity Value Units Method Reference Comment
Deltar1435. ± 11.kJ/molG+TSHu, Hill, et al., 1997gas phase; Calculations imply singlet carbene in anion, triplet in phenol
Quantity Value Units Method Reference Comment
Deltar1406. ± 10.kJ/molCIDCHu, Hill, et al., 1997gas phase; Calculations imply singlet carbene in anion, triplet in phenol

C5H5O2- + Hydrogen cation = C5H6O2

By formula: C5H5O2- + H+ = C5H6O2

Quantity Value Units Method Reference Comment
Deltar1641. ± 18.kJ/molG+TSSachs and Kass, 1994gas phase; Between water and fluorobenzene. Site of protonation uncertain.
Quantity Value Units Method Reference Comment
Deltar1608. ± 17.kJ/molIMRBSachs and Kass, 1994gas phase; Between water and fluorobenzene. Site of protonation uncertain.

C7H5O3- + Hydrogen cation = Benzoic acid, 4-hydroxy-

By formula: C7H5O3- + H+ = C7H6O3

Quantity Value Units Method Reference Comment
Deltar1405. ± 8.8kJ/molG+TSKebarle and McMahon, 1977gas phase; This is probably the phenolic site acidity, not the carboxylic.
Quantity Value Units Method Reference Comment
Deltar1376. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase; This is probably the phenolic site acidity, not the carboxylic.

C7H7O- + Hydrogen cation = Benzyl alcohol

By formula: C7H7O- + H+ = C7H8O

Quantity Value Units Method Reference Comment
Deltar1548. ± 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
Deltar1520. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale

C6F5O- + Hydrogen cation = Phenol, pentafluoro-

By formula: C6F5O- + H+ = C6HF5O

Quantity Value Units Method Reference Comment
Deltar1372. ± 9.2kJ/molG+TSKoppel, Taft, et al., 1994gas phase
Deltar<1630. ± 11.kJ/molAcidBriscese and Riveros, 1975gas phase; HO- + C6F6 -> , acidity probably ca. 320 kcal
Quantity Value Units Method Reference Comment
Deltar1342. ± 8.4kJ/molIMREKoppel, Taft, et al., 1994gas phase

C8H5- + Hydrogen cation = Phenylethyne

By formula: C8H5- + H+ = C8H6

Quantity Value Units Method Reference Comment
Deltar1551. ± 9.6kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1518. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale

CH2NS- + Hydrogen cation = CH3NS

By formula: CH2NS- + H+ = CH3NS

Quantity Value Units Method Reference Comment
Deltar1464. ± 15.kJ/molG+TSKass and DePuy, 1985gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1436. ± 15.kJ/molIMRBKass and DePuy, 1985gas phase; value altered from reference due to change in acidity scale

C2H2D5O- + Hydrogen cation = C2H3D3O

By formula: C2H2D5O- + H+ = C2H3D3O

Quantity Value Units Method Reference Comment
Deltar1580. ± 9.6kJ/molG+TSDang, Motell, et al., 1993gas phase; CIDC in SIFT at 30 V: 0.20 ± 0.15 kcal/mol weaker than protio
Quantity Value Units Method Reference Comment
Deltar1552. ± 9.2kJ/molCIDCDang, Motell, et al., 1993gas phase; CIDC in SIFT at 30 V: 0.20 ± 0.15 kcal/mol weaker than protio

C7H7- + Hydrogen cation = 2,5-Norbornadiene

By formula: C7H7- + H+ = C7H8

Quantity Value Units Method Reference Comment
Deltar1672. ± 7.5kJ/molG+TSLee and Squires, 1986gas phase; Between EtNH2, nPrNH2
Quantity Value Units Method Reference Comment
Deltar1637. ± 6.3kJ/molIMRBLee and Squires, 1986gas phase; Between EtNH2, nPrNH2
Deltar1628. ± 21.kJ/molIMRBWright and Beauchamp, 1981gas phase

HN2O- + Hydrogen cation = H2N2O

By formula: HN2O- + H+ = H2N2O

Quantity Value Units Method Reference Comment
Deltar1513. ± 9.6kJ/molG+TSSheldon, Ohair, et al., 1995gas phase; Acidity between PhCOMe, HCONHMe, near CF3CH2OH. Acid: H2N-NO
Quantity Value Units Method Reference Comment
Deltar1482. ± 8.4kJ/molIMRBSheldon, Ohair, et al., 1995gas phase; Acidity between PhCOMe, HCONHMe, near CF3CH2OH. Acid: H2N-NO

C14H9CrF6- + Hydrogen cation = C14H10CrF6

By formula: C14H9CrF6- + H+ = C14H10CrF6

Quantity Value Units Method Reference Comment
Deltar1487. ± 11.kJ/molG+TSKahn, Hehre, et al., 1984gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1457. ± 10.kJ/molIMREKahn, Hehre, et al., 1984gas phase; value altered from reference due to change in acidity scale

C14H9CrF6- + Hydrogen cation = C14H10CrF6

By formula: C14H9CrF6- + H+ = C14H10CrF6

Quantity Value Units Method Reference Comment
Deltar1490. ± 11.kJ/molG+TSKahn, Hehre, et al., 1984gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1459. ± 10.kJ/molIMREKahn, Hehre, et al., 1984gas phase; value altered from reference due to change in acidity scale

C7H6NO3- + Hydrogen cation = Phenol, 3-methyl-4-nitro-

By formula: C7H6NO3- + H+ = C7H7NO3

Quantity Value Units Method Reference Comment
Deltar1380. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1350. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale

C8H11O- + Hydrogen cation = 2-Cyclohexen-1-one, 4,4-dimethyl-

By formula: C8H11O- + H+ = C8H12O

Quantity Value Units Method Reference Comment
Deltar1529. ± 8.8kJ/molG+TSBartmess and Kiplinger, 1986gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1497. ± 8.4kJ/molIMREBartmess and Kiplinger, 1986gas phase; value altered from reference due to change in acidity scale

C7H7- + Hydrogen cation = Tetracyclo[3.2.0.0(2,7).0(4,6)]heptane

By formula: C7H7- + H+ = C7H8

Quantity Value Units Method Reference Comment
Deltar1686. ± 4.2kJ/molD-EAGunion, Karney, et al., 1996gas phase; Assignment of 1- and 2- isomers uncertain.
Deltar1685.6 ± 3.8kJ/molG+TSLee, DePuy, et al., 1996gas phase
Quantity Value Units Method Reference Comment
Deltar1651.4 ± 3.3kJ/molIMRELee, DePuy, et al., 1996gas phase

C9H19O- + Hydrogen cation = 3-Pentanol, 2,2,4,4-tetramethyl-

By formula: C9H19O- + H+ = C9H20O

Quantity Value Units Method Reference Comment
Deltar1538. ± 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. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale

C7H7O2S- + Hydrogen cation = C7H8O2S

By formula: C7H7O2S- + H+ = C7H8O2S

Quantity Value Units Method Reference Comment
Deltar1427. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1399. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale

C7H7O2S- + Hydrogen cation = C7H8O2S

By formula: C7H7O2S- + H+ = C7H8O2S

Quantity Value Units Method Reference Comment
Deltar1412. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1383. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale

C7H7O3S- + Hydrogen cation = C7H8O3S

By formula: C7H7O3S- + H+ = C7H8O3S

Quantity Value Units Method Reference Comment
Deltar1406. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1377. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale

C7H7O3S- + Hydrogen cation = C7H8O3S

By formula: C7H7O3S- + H+ = C7H8O3S

Quantity Value Units Method Reference Comment
Deltar1385. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1356. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale

C13H9O2- + Hydrogen cation = m-Hydroxybenzophenone

By formula: C13H9O2- + H+ = C13H10O2

Quantity Value Units Method Reference Comment
Deltar1428. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1400. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale

C9H5N2- + Hydrogen cation = Acetonitrile, 2-(3-cyanophenyl)-

By formula: C9H5N2- + H+ = C9H6N2

Quantity Value Units Method Reference Comment
Deltar1419. ± 9.6kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1390. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale

C5H10NO2- + Hydrogen cation = C5H11NO2

By formula: C5H10NO2- + H+ = C5H11NO2

Quantity Value Units Method Reference Comment
Deltar1486. ± 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
Deltar1458. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale

C6H11S2- + Hydrogen cation = C6H12S2

By formula: C6H11S2- + H+ = C6H12S2

Quantity Value Units Method Reference Comment
Deltar1565. ± 8.8kJ/molG+TSBartmess, Hays, et al., 1981gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1535. ± 8.4kJ/molIMREBartmess, Hays, et al., 1981gas phase; value altered from reference due to change in acidity scale

C6H3Cl2O- + Hydrogen cation = Phenol, 3,5-dichloro-

By formula: C6H3Cl2O- + H+ = C6H4Cl2O

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
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

C6H2Cl3O- + Hydrogen cation = Phenol, 3,4,5-trichloro-

By formula: C6H2Cl3O- + H+ = C6H3Cl3O

Quantity Value Units Method Reference Comment
Deltar1384. ± 9.2kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1355. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale

cyclohexenone-4-enolate anion + Hydrogen cation = 2-Cyclohexen-1-one

By formula: C6H7O- + H+ = C6H8O

Quantity Value Units Method Reference Comment
Deltar1496. ± 8.8kJ/molG+TSBartmess and Kiplinger, 1986gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1464. ± 8.4kJ/molIMREBartmess and Kiplinger, 1986gas phase; value altered from reference due to change in acidity scale

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.

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]

Caldwell, McMahon, et al., 1985
Caldwell, G.; McMahon, T.B.; Kebarle, P.; Bartmess, J.E.; Kiplinger, J.P., Methyl substituent effects in the gas phase acidities of halosubstituted oxygen acids. A realignment with substituent effects in solution, J. Am. Chem. Soc., 1985, 107, 80. [all data]

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

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

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]

DePuy, Bierbaum, et al., 1980
DePuy, C.H.; Bierbaum, V.M.; Flippin, L.A.; Brabowski, J.J.; King, G.K.; Schmidt, R.J.; Sullivan, S.A., Gas phase reactions of anions with substituted silanes, J. Am. Chem. Soc., 1980, 102, 5012. [all data]

Cooper and Compton, 1973
Cooper, C.D.; Compton, R.N., Electron attachment and cesium collisional ionization studies of tetrafluorosuccinic and hexafluoroglutaric anhydrides: Molecular electron affinities, J. Chem. Phys., 1973, 59, 3550. [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]

Kato, Gareyev, et al., 1998
Kato, S.; Gareyev, R.; DePuy, C.H.; Bierbaum, V.M., Structures, energetics, and chemical reactions of anions derived from cyclooctatetraene, J. Am. Chem. Soc., 1998, 120, 20, 5033-5042, https://doi.org/10.1021/ja972628o . [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]

Reed, Kass, et al., 2002
Reed, D.R.; Kass, S.R.; Mondanaro, K.R.; Dailey, W.P., Formation of a 1-bicyclo[1.1.1]pentyl anion and an experimental determination of the acidity and C-H bond dissociation energy of 3-tert-butylbicyclo[1.1.1]pentane, J. Am. Chem. Soc., 2002, 124, 11, 2790-2795, https://doi.org/10.1021/ja0121890 . [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]

Jinfeng, Topsom, et al., 1988
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]

Pabst, Margrave, et al., 1977
Pabst, R.E.; Margrave, J.L.; Franklin, J.L., Electron impact studies of the tetrachlorides and tetrabromides of silicon and germanium, Int. J. Mass Spectrom. Ion Phys., 1977, 25, 361. [all data]

Koppel, Mishima, et al., 1993
Koppel, I.A.; Mishima, M.; Stock, L.M.; Taft, R.W.; Topsom, R.D., Acidities of 4-Substituted Benzoic, Bicyclo[2.2.2]Oct-1-yl and Bicyclo[2.2.2]Oct-2-enyl Carboxylic Acids, J. Phys. Org. Chem., 1993, 6, 12, 685, https://doi.org/10.1002/poc.610061205 . [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]

Hu, Hill, et al., 1997
Hu, J.; Hill, B.T.; Squires, R.R., New Approach to Carbene Chemistry, via Distonic Carbene Ions. A Case of Spin-Forbidden Proton Transfer and Carbene-Biradical Tautomerism, J. Am. Chem. Soc., 1997, 119, 48, 11699, https://doi.org/10.1021/ja9727070 . [all data]

Sachs and Kass, 1994
Sachs, R.K.; Kass, S.R., 3-Carbomethoxycyclopropen-3-yl Anion - Formation and Characterization of an Antiaromatic Ion, J. Am. Chem. Soc., 1994, 116, 2, 783, https://doi.org/10.1021/ja00081a055 . [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]

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]

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

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

Dang, Motell, et al., 1993
Dang, T.T.; Motell, E.L.; Travers, M.J.; Clifford, E.P.; Ellison, G.B.; Depuy, C.H.; Bierbaum, V.M., Experimental and Computational Studies of Deuterated Ethanols - Gas-Phase Acidities, Electron Affinities and Bond Dissociation Energies, Int. J. Mass Spectrom. Ion Proc., 1993, 123, 3, 171, https://doi.org/10.1016/0168-1176(93)87096-B . [all data]

Lee and Squires, 1986
Lee, R.E.; Squires, R.R., Anionic homoaromaticity: A gas phase experimental study, J. Am. Chem. Soc., 1986, 105, 5078. [all data]

Wright and Beauchamp, 1981
Wright, C.A.; Beauchamp, J.L., Infrared spectra of gas phase ions and their use in elucidating reaction mechanisms. Identification of C7H7- structural isomers by multiphoton electron detachment using a low-powered laser, J. Am. Chem. Soc., 1981, 103, 6499. [all data]

Sheldon, Ohair, et al., 1995
Sheldon, J.C.; Ohair, R.A.J.; Downard, K.M.; Gronert, S.; Krempp, M.; Depuy, C.H.; Bowie, J.H., A potential surface map of the H-/N2O system. The gas phase ion chemistry of HN2O-, Aust. J. Chem., 1995, 48, 155. [all data]

Kahn, Hehre, et al., 1984
Kahn, S.D.; Hehre, W.J.; Bartmess, J.E.; Caldwell, G., Effect of Metal Complexation on the Gas-phase Acidities of Alkylbenzenes, Organomet., 1984, 3, 11, 1740, https://doi.org/10.1021/om00089a024 . [all data]

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

Bartmess and Kiplinger, 1986
Bartmess, J.E.; Kiplinger, J.P., 'Kinetic' vs. thermodynamic acidities of enones in the gas phase, J. Org. Chem., 1986, 51, 2173. [all data]

Gunion, Karney, et al., 1996
Gunion, R.F.; Karney, W.; Wenthold, P.G.; Borden, W.T.; Lineberger, W.C., Ultraviolet Photoelectron Spectroscopy of Some C7H7- Isomers: Quadricyclanide, Norbornadienide, Cycloheptatrienide, and 1,6-Heptadiynide, J. Am. Chem. Soc., 1996, 118, 21, 5074, https://doi.org/10.1021/ja954026f . [all data]

Lee, DePuy, et al., 1996
Lee, H.S.; DePuy, C.H.; Bierbaum, V.M., Reactivity and Thermochemistry of Quadricyclane in the Gas Phase, J. Am. Chem. Soc., 1996, 118, 21, 5068, https://doi.org/10.1021/ja9540278 . [all data]

Bartmess, Hays, et al., 1981
Bartmess, J.E.; Hays, R.L.; Khatri, H.N.; Misra, R.N.; Wilson, S.W., Elimination, fragmentation and proton transfer in 1,3-dithianes and 1,3-dithiolanes in the gas phase, J. Am. Chem. Soc., 1981, 103, 4746. [all data]


Notes

Go To: Top, Reaction thermochemistry data, References