메뉴 건너뛰기




Volumn 119, Issue 20, 1997, Pages 4686-4697

Absolute heats of formation of phenylcarbene and vinylcarbene

Author keywords

[No Author keywords available]

Indexed keywords

ANION; BENZENE DERIVATIVE; HALIDE; PHENYLCARBENE; UNCLASSIFIED DRUG; VINYL DERIVATIVE; VINYLCARBENE;

EID: 0030949567     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963918s     Document Type: Article
Times cited : (57)

References (109)
  • 9
    • 0003610749 scopus 로고
    • Liebman, J. F., Greenberg, A., Eds.; VCH Publishers Inc.: Deerfield Beach FL, Chapter 3
    • (e) Liebman, J. F.; Simons, J. In Molecular Structure and Energetics; Liebman, J. F., Greenberg, A., Eds.; VCH Publishers Inc.: Deerfield Beach FL, 1986; Vol. 1, Chapter 3.
    • (1986) Molecular Structure and Energetics , vol.1
    • Liebman, J.F.1    Simons, J.2
  • 11
    • 0040854586 scopus 로고
    • Carter, E. A.; Goddard, W. A., III. J. Phys. Chem. 1986, 90, 998. See also: Simons, J. Nature 1965, 205, 1308.
    • (1965) Nature , vol.205 , pp. 1308
    • Simons, J.1
  • 13
    • 1842346235 scopus 로고
    • All data taken from the NIST Negative Ion Energetics Database, Version 3.00, NIST Standard Reference Database 19B, October 1993
    • Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. D. J. Phys. Chem. Ref. Data 1988, 17, Suppl. 1. All data taken from the NIST Negative Ion Energetics Database, Version 3.00, NIST Standard Reference Database 19B, October 1993.
    • (1988) J. Phys. Chem. Ref. Data , vol.17 , Issue.1 SUPPL.
    • Lias, S.G.1    Bartmess, J.E.2    Liebman, J.F.3    Holmes, J.L.4    Levin, R.D.5    Mallard, W.D.6
  • 18
    • 1842552591 scopus 로고    scopus 로고
    • In press
    • (a) Poutsma, J. C.; Paulino, J. A.; Squires, R. R. J. Phys. Chem. In press. For preliminary values, see: Paulino, J. A.; Squires, R. R. J. Am. Chem. Soc. 1991, 113, 1845. Paulino, J. A. Ph.D. Thesis, Purdue University, 1992.
    • J. Phys. Chem.
    • Poutsma, J.C.1    Paulino, J.A.2    Squires, R.R.3
  • 19
    • 1842552591 scopus 로고    scopus 로고
    • (a) Poutsma, J. C.; Paulino, J. A.; Squires, R. R. J. Phys. Chem. In press. For preliminary values, see: Paulino, J. A.; Squires, R. R. J. Am. Chem. Soc. 1991, 113, 1845. Paulino, J. A. Ph.D. Thesis, Purdue University, 1992.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 1845
    • Paulino, J.A.1    Squires, R.R.2
  • 20
    • 1842552591 scopus 로고    scopus 로고
    • Ph.D. Thesis, Purdue University
    • (a) Poutsma, J. C.; Paulino, J. A.; Squires, R. R. J. Phys. Chem. In press. For preliminary values, see: Paulino, J. A.; Squires, R. R. J. Am. Chem. Soc. 1991, 113, 1845. Paulino, J. A. Ph.D. Thesis, Purdue University, 1992.
    • (1992)
    • Paulino, J.A.1
  • 47
    • 0001136058 scopus 로고
    • and references therein
    • Platz, M. S. Acct. Chem Res. 1995, 28, 487 and references therein.
    • (1995) Acct. Chem Res. , vol.28 , pp. 487
    • Platz, M.S.1
  • 62
    • 1842312678 scopus 로고    scopus 로고
    • Analysis carried out using the CRUNCH program developed by P. B. Armentrout and K. M. Ervin
    • Analysis carried out using the CRUNCH program developed by P. B. Armentrout and K. M. Ervin.
  • 65
    • 1842360895 scopus 로고    scopus 로고
    • note
    • Bending frequencies were obtained by loosening the carbon-halide bending modes in the reactant anions by factors between 2 and 10. Threshold curves were fit with assumed transition states corresponding to activation entropies that were 2 eu higher and 2 eu lower than the ones used in the final analysis. The effect on the threshold energies was less than or equal to 1 kcal/mol for all three halobenzyl anion dissociations.
  • 66
    • 85005470381 scopus 로고
    • We employed an average scale factor of 0.9 because some of the calculated frequencies were analytically derived while others were numerically evaluated. This value is in the range of the one recommended by Pople and Radom for HF/6-31G* frequencies. Pople, J. A.; Scott, A. P.; Wong, M. W.; Radom, L. Isr. J. Chem. 1993, 33, 345.
    • (1993) Isr. J. Chem. , vol.33 , pp. 345
    • Pople, J.A.1    Scott, A.P.2    Wong, M.W.3    Radom, L.4
  • 67
    • 1842353132 scopus 로고    scopus 로고
    • note
    • The active orbital spaces for these calculations consisted of the nonbonding σ and π orbitals of each carbene. A single reference configuration was used for the triplet states (i.e., ROHF/6-31G*). and a two-configuration reference was used for each singlet state (i.e. TCSCF/6-31G*).
  • 82
    • 1842305986 scopus 로고    scopus 로고
    • note
    • The energy-resolved cross section obtained with argon target is similar in appearance, although it displays somewhat more tailing in the threshold region. Because of the greater spread in the lab-frame collision energies when neon compared to argon target is used, the former is preferred for energy-resolved analysis of low-dissociation energy reactions.
  • 84
    • 1842348181 scopus 로고    scopus 로고
    • note
    • Translational and rotational contributions to the heat capacity are treated classically, and the vibrational components were obtained from calculated vibrational frequencies.
  • 87
    • 33645047765 scopus 로고    scopus 로고
    • Methyl chloride: Smith, B. J.; Radom, L. J. Phys. Chem. 1991, 95, 10549. Methyl bromide: Mayer, P. A.; Radom, L. Personal communication of unpublished results.
    • (1991) J. Phys. Chem. , vol.95 , pp. 10549
    • Smith, B.J.1    Radom, L.2
  • 88
    • 33645047765 scopus 로고    scopus 로고
    • Personal communication of unpublished results
    • Methyl chloride: Smith, B. J.; Radom, L. J. Phys. Chem. 1991, 95, 10549. Methyl bromide: Mayer, P. A.; Radom, L. Personal communication of unpublished results.
    • Mayer, P.A.1    Radom, L.2
  • 90
    • 1842274260 scopus 로고    scopus 로고
    • note
    • The 1-bromoallyl anion was also generated by proton abstraction from 1-bromopropene; the behavior of bromoallyl ions produced from the two different precursors is identical.
  • 91
    • 1842358937 scopus 로고    scopus 로고
    • note
    • The 1-halopropenes are 1-2 kcal/mol lower in energy than the 3-halopropene isomers (ref 5), which means that the 3-position in a 1-haloallyl anion is the thermodynamically preferred site of protonation.
  • 94
    • 0002302717 scopus 로고
    • Bowers, M. T., Ed.; Academic Press: New York, Chapter 11
    • Bartmess, J. E.; McIver, R. T., Jr. In Gas Phase Ion Chemistry; Bowers, M. T., Ed.; Academic Press: New York, 1979; Vol. 2, Chapter 11.
    • (1979) Gas Phase Ion Chemistry , vol.2
    • Bartmess, J.E.1    McIver Jr., R.T.2
  • 96
    • 1842352108 scopus 로고    scopus 로고
    • note
    • A concise description of these calculations can be found in ref 56. Note that the first term of eq A2 in this paper contains a minor typographical error, it should read 5/2R ln(T).
  • 106
    • 0004344770 scopus 로고
    • Benjamin/Cummings Publishing Co.: Menlo Park, CA, Chapter 7
    • Turro, N. J. Modern Molecular Photochemistry, Benjamin/Cummings Publishing Co.: Menlo Park, CA, 1978; Chapter 7.
    • (1978) Modern Molecular Photochemistry
    • Turro, N.J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.