SCOPUS 정보 검색 플랫폼

Volumn 67, Issue 9, 2002, Pages 3079-3088

Computational and experimental studies of the effect of substituents on the singlet-triplet energy gap in phenyl(carbomethoxy)carbene

(6) Geise, C Michael a Wang, Yuhong b Mykhaylova, Olena a,c Frink, Brian T c Toscano, John P b Hadad, Christopher M a

a OHIO STATE UNIVERSITY (United States)

b JOHNS HOPKINS UNIVERSITY (United States)

c Lakeland University (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ELECTRONIC PROPERTIES; ENERGY GAP; FREE ENERGY; GROUND STATE; INFRARED SPECTROSCOPY; PERTURBATION TECHNIQUES; SOLVENTS; SUBSTITUTION REACTIONS;

LINEAR FREE ENERGY (LFE); TIME-RESOLVED INFRARED (TRIR) SPECTROSCOPY;

AROMATIC HYDROCARBONS;

CARBENOID; PHENYL(CARBOMETHOXY)CARBENE; UNCLASSIFIED DRUG;

ARTICLE; ENERGY TRANSFER; GAS; INFRARED SPECTROSCOPY; MATHEMATICAL ANALYSIS; SOLVATION;

EID: 84962428324 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo0255330 Document Type: Article

Times cited : (48)

References (108)

1
- 84917970653
- (1902) Justus Leibigs Ann. Chem. , vol.325 , pp. 129
- Wolff, L.¹

2
- 1542706505
- (1912) Justus Liebigs Ann. Chem. , vol.394 , pp. 23
- Wolff, L.¹

3
- 0000709206
- (1994) Chem. Rev. , vol.94 , pp. 1091
- Ye, T.¹ McKervey, A.M.²

4
- 0003905801
- Academic Press: Orlando, FL
- (1986) Diazo Compounds
- Regitz, M.¹ Maas, G.²

5
- 84982385017
- (1975) Angew. Chem., Int. Ed. Engl. , vol.14 , pp. 32
- Meier, H.¹ Zeller, K.-P.²

6
- 0003428791
- Wiley: New York
- (1973) Carbenes , vol.1-2
- Jones M., Jr.¹ Moss, R.A.²

7
- 0004050551
- Academic Press: New York
- (1971) Carbene Chemistry, 2nd ed.
- Kirmse, W.¹

8
- 0003467672
- Wiley: New York
- (1992) Advanced Organic Chemistry , pp. 1083
- March, J.¹

9
- 0028972693
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 10635
- Nakatani, K.¹ Maekawa, S.² Tanabe, K.³ Saito, I.⁴

10
- 0030884569
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 7626
- Nakatani, K.¹ Shirai, J.² Sando, S.³ Saito, I.⁴

11
- 0024737386
- (1989) Chem. Rev. , vol.89 , pp. 1273
- Reichmanis, E.¹ Thompson, L.F.²

12
- 0004175815
- Wiley: New York
- (1989) Photoreactive Polymers: The Science and Technology of Resists
- Reiser, A.¹

13
- 0003518370
- Academic Press: San Diego
- (1993) Polymers for Electronic and Photonic Applications
- Wong, C.P.¹

14
- 0001440236
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 7034
- Modarelli, D.A.¹ Morgan, S.² Platz, M.S.³

15
- 33751391630
- (1992) J. Org. Chem. , vol.57 , pp. 2841
- White W.R. III¹ Platz, M.S.²

16
- 0030996428
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 3580
- Butterbaugh, J.S.¹ Toscano, J.P.² Weaver, W.L.³ Gord, J.R.⁴ Gustafson, T.L.⁵ Hadad, C.M.⁶ Platz, M.S.⁷

17
- 0000241299
- Brinker, U.H., Ed.; JAI Press: Greenwich CT
- (1998) Advances in Carbene Chemistry , vol.2 , pp. 133
- Platz, M.S.¹

18
- 0001447626
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 454
- Tomioka, H.¹ Hayashi, N.² Izawa, Y.³ Liu, M.T.H.⁴

19
- 0029992211
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 3829
- Bonneau, R.¹ Liu, M.T.H.² Kim, K.C.³ Goodman, J.L.⁴

20
- 0001965020
- Brinker, U.H., Ed.; JAI Press: Greenwich CT
- (1998) Advances in Carbene Chemistry , vol.2 , pp. 1
- Bonneau, R.¹ Liu, M.T.H.²

21
- 0029744771
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 7229
- Bonneau, R.¹ Liu, M.T.H.²

22
- 0008881731
- (1984) Tetrahedron Lett. , vol.25 , pp. 4211
- Warner, P.M.¹

23
- 0000456835
- (1983) J. Am. Chem. Soc. , vol.105 , pp. 6488
- Ahmed, S.N.¹ Shevlin, P.B.²

24
- 0033523262
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 7150
- Xu, G.¹ Chang, T.-M.² Zhou, J.³ McKee, M.L.⁴ Shevlin, P.B.⁵

25
- 0000943065
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 5049
- Mueller, P.H.¹ Rondan, N.G.² Houk, K.N.³ Harrison, J.F.⁴ Hooper, D.⁵ Willen, B.H.⁶ Liebman, J.F.⁷

26
- 33947094323
- (1978) J. Am. Chem. Soc. , vol.100 , pp. 1333
- Baird, N.C.¹ Taylor, K.F.²

27
- 37049130629
- (1970) J. Chem. Soc., Chem. Commun. , pp. 792
- Bethell, D.¹ Stevens, G.² Tickle, P.³

28
- 0002551859
- (1971) J. Chem. Soc. B , pp. 23
- Bethell, D.¹ Newall, A.R.² Whittaker, D.³

29
- 37049139465
- (1974) J. Chem. Soc., Perkin Trans. 2 , pp. 1307
- Bethell, D.¹ Hayes, J.² Newall, A.R.³

30
- 0021119808
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 198
- Griller, D.¹ Nazran, A.S.² Scaiano, J.C.³

31
- 0033620447
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 2863
- Zhu, Z.¹ Bally, T.² Stracener, L.L.³ McMahon, R.J.⁴

32
- 0033620462
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 2875
- Wang, Y.¹ Yuzawa, T.² Hamaguchi, H.³ Toscano, J.P.⁴

33
- 85052617268
- (2001) Adv. Photochem. , vol.26 , pp. 41
- Toscano, J.P.¹

34
- 0033620429
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 2883
- Wang, J.-L.¹ Likhotvorik, I.² Platz, M.S.³

35
- 0037181054
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 1761
- Wang, Y.¹ Hadad, C.M.² Toscano, J.P.³

36
- 0034553421
- (2000) J. Org. Chem. , vol.65 , pp. 8348
- Geise, C.M.¹ Hadad, C.M.²

37
- 0000757043
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 9787
- Cramer, C.J.¹ Dulles, F.J.² Falvey, D.E.³

38
- 0026524153
- (1992) Tetrahedron Lett. , vol.33 , pp. 1705
- Falvey, D.E.¹ Cramer, C.J.²

39
- 0000206012
- (1996) J. Phys. Chem. , vol.100 , pp. 14028
- Michalak, J.¹ Zhai, H.B.² Platz, M.S.³

40
- 0000436545
- (1997) J. Phys. Org. Chem. , vol.10 , pp. 755
- Worthington, S.E.¹ Cramer, C.J.²

41
- 0001743567
- (1998) J. Phys. Chem. A , vol.102 , pp. 2732
- Gonzalez, C.¹ Restrepo-Cossio, A.² Marquez, M.³ Wiberg, K.B.⁴ De Rosa, M.⁵

42
- 0032545009
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 11778
- Sullivan, M.B.¹ Brown, K.² Cramer, C.J.³ Truhlar, D.G.⁴

43
- 0001030275
- (1999) J. Phys. Chem. A , vol.103 , pp. 6191
- Marquez, M.¹ Mari, F.² Gonzalez, C.A.³

44
- 0003442182
- Springer: New York
- (1991) Density Functional Methods in Chemistry
- Labanowski, J.W.¹ Andzelm, J.²

45
- 0003569570
- Oxford University Press: New York
- (1989) Density Functional Theory in Atoms and Molecules
- Parr, R.G.¹ Yang, W.²

46
- 4243553426
- (1988) Phys. Rev. A , vol.38 , pp. 3098
- Becke, A.D.¹

47
- 34250817103
- (1993) J. Chem. Phys. , vol.98 , pp. 1372
- Becke, A.D.¹

48
- 0345491105
- (1988) Phys. Rev. B , vol.37 , pp. 785
- Lee, C.¹ Yang, W.² Parr, R.G.³

49
- 33748545144
- (1973) Theor. Chim. Acta , vol.28 , pp. 213
- Hariharan, P.C.¹ Pople, J.A.²

50
- 0011083273
- (1996) J. Phys. Chem. , vol.100 , pp. 16502
- Scott, A.P.¹ Radom, L.²

51
- 84873055189
- John Wiley & Sons: New York
- (1986) Ab initio Molecular Orbital Theory
- Hehre, W.J.¹ Radom, L.² Schleyer, P.V.R.³ Pople, J.A.⁴

52
- 0000340764
- (1999) J. Chem. Phys. , vol.110 , pp. 2822
- Montgomery J.A., Jr.¹ Frisch, M.J.² Ochterski, J.W.³ Petersson, G.A.⁴

54
- 0000698918
- (1987) Synth. Commun. , vol.17 , pp. 1709
- Baum, J.S.¹ Shook, D.A.² Davies, H.M.L.³ Smith, H.D.⁴

55
- 0001405856
- (1991) J. Org. Chem. , vol.56 , pp. 3817
- Davies, H.M.L.¹ Clark, T.J.² Smith, H.D.³

56
- 0025522250
- (1990) Appl. Spectrosc. , vol.44 , pp. 1431
- Iwata, K.¹ Hamaguchi, H.²

57
- 0000599399
- (1994) Appl. Spectrosc. , vol.48 , pp. 684
- Yuzawa, T.¹ Kato, C.² George, M.W.³ Hamaguchi, H.⁴

58
- 0001501228
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 5390
- Kim, K.S.¹ Schaefer H.F. III²

59
- 0001545523
- (1991) Can. J. Chem. , vol.69 , pp. 1630
- Gosavi, R.K.¹ Torres, M.² Strausz, O.P.³

60
- 0001620087
- (1996) Mol. Phys. , vol.87 , pp. 389
- Xie, Y.¹ Schaefer H.F. III²

61
- 0034826747
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 6069
- Scott, A.P.¹ Platz, M.S.² Radom, L.³

62
- 33845282074
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 5935
- Wiberg, K.B.¹ Laidig, K.E.²

63
- 0033410355
- (1999) Theor. Chem. Acc. , vol.102 , pp. 272
- Bohn, R.K.¹ Wiberg, K.B.²

64
- 0001651476
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 1870
- Wang, X.¹ Houk, K.N.²

65
- 33845278614
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 1872
- Wiberg, K.B.¹ Laidig, K.E.²

66
- 0001482287
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 10630
- Evanseck, J.D.¹ Houk, K.N.² Briggs, J.M.³ Jorgensen, W.L.⁴

67
- 0037116511
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 355
- Geise, C.M.¹ Hadad, C.M.² Zheng, F.³ Shevlin, P.B.⁴

68
- 0034706005
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 8087
- Hess, G.C.¹ Kohler, B.² Likhotvorik, I.³ Peon, J.⁴ Platz, M.S.⁵

69
- 0003595276
- Brooks/Cole: Pacific Grove
- (1998) Perspectives on Structure and Mechanism in Organic Chemistry , pp. 390
- Carroll, F.A.¹

70
- 0003558028
- John Wiley and Sons: New York
- (1963) Rates and Equilibria of Organic Reactions , pp. 71
- Leffler, J.E.¹ Gurnwald, E.²

71
- 0003568380
- Lewis, E.S., Ed.; Wiley-Interscience: New York
- (1974) Investigation of Rates and Mechanisms of Reactions, 3rd ed. , Issue.PART I , pp. 777
- Fuchs, R.¹ Lewis, E.S.²

72
- 0001703066
- (1987) J. Chem. Educ. , vol.64 , pp. 475
- Buncel, E.¹ Wilson, H.²

73
- 0002801544
- (1937) J. Am. Chem. Soc. , vol.59 , pp. 96
- Hammett, L.P.¹

74
- 33747866218
- (1935) Chem. Rev. , vol.17 , pp. 125
- Hammett, L.P.¹

75
- 0542443644
- (1953) Chem. Rev. , vol.53 , pp. 191
- Jaffe, H.H.¹

76
- 0004263533
- Cambridge University Press: Cambridge, England
- (1973) The Hammett Equation
- Johnson, C.D.¹

77
- 0001141360
- (1979) Can. J. Chem. , vol.57 , pp. 2652
- Humphreys, R.W.R.¹ Arnold, D.R.²

78
- 0001686523
- (1983) J. Am. Chem. Soc. , vol.105 , pp. 2912
- Nazran, A.S.¹ Gabe, E.J.² LePage, Y.³ Northcott, D.J.⁴ Park, J.M.⁵ Griller, D.⁶

79
- 0000756537
- (1984) J. Phys. Chem. , vol.88 , pp. 5251
- Nazran, A.S.¹ Lee, F.L.² Gable, E.J.³ LePage, Y.⁴ Northcott, D.J.⁵ Park, J.M.⁶ Griller, D.⁷

80
- 37049103406
- (1983) J. Chem. Soc., Chem. Commun. , pp. 850
- Nazran, A.S.¹ Griller, D.²

81
- 0001387304
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 7692
- Tomioka, H.¹ Hirai, K.² Tobayashi, K.³ Murata, S.⁴ Izawa, Y.⁵ Inagaki, S.⁶ Okajima, T.⁷

82
- 37049095025
- (1980) J. Chem. Soc., Perkin Trans. 2 , pp. 1636
- Tomioka, H.¹ Okuno, H.² Izawa, Y.³

83
- 0001510656
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 1942
- Fujiwara, Y.¹ Tanimoto, Y.² Itoh, M.³ Hirai, K.⁴ Tomioka, H.⁵

84
- 0042440143
- (1958) J. Org. Chem. , vol.23 , pp. 420
- McDaniel, D.H.¹ Brown, H.C.²

85
- 0004028219
- Newman, M.S., Ed.; John Wiley & Sons: New York
- (1956) Steric Effects in Organic Chemistry
- Taft, R.W.¹

86
- 0006226243
- (1970) Quart. Rev. Chem. Soc. , vol.24 , pp. 433
- Shorter, J.¹

87
- 0001407172
- (1978) J. Org. Chem. , vol.43 , pp. 3095
- Bordwell, F.G.¹ Bartmess, J.E.² Hautala, J.A.³

88
- 78349286235
- (1964) Prog. Phys. Org. Chem. , vol.2 , pp. 323
- Ritchie, C.D.¹ Sager, W.F.²

89
- 11744256643
- (1994) Chem. Rev. , vol.94 , pp. 2027
- Tomasi, J.¹ Persico, M.²

90
- 84946893847
- (1981) Chem. Phys. , vol.55 , pp. 117
- Miertus, S.¹ Scrocco, E.² Tomasi, J.³

91
- 84986435825
- (1995) J. Comput. Chem. , vol.16 , pp. 1449
- Cammi, R.¹ Tomasi, J.²

92
- 84962359221
- (1996) Chem. Phys. Lett. , vol.255 , pp. 327
- Cossi, M.¹ Barone, V.² Cammi, R.³ Tomasi, J.⁴

93
- 84962476304
- (1998) Adv. Quantum Chem. , vol.32 , pp. 227
- Amovilli, C.¹ Barone, V.² Cammi, R.³ Cancès, E.⁴ Cossi, M.⁵ Menucci, B.⁶ Pommelli, C.S.⁷

94
- 84961981091
- (1999) Chem. Rev. , vol.99 , pp. 2161
- Cramer, C.J.¹ Truhlar, D.G.²

95
- 33751121669
- (1991) Angew. Chem., Int. Ed. Engl. , vol.30 , pp. 1366
- Chiang, Y.¹ Kresge, A.J.² Pruszynski, P.³ Schepp, N.P.⁴ Wirz, J.⁵

96
- 84962435373
- Ph.D Dissertation, University of Fribourg, Switzerland
- (1997)
- Zhu, Z.¹

97
- 0001141931
- (1976) J. Am. Chem. Soc. , vol.98 , pp. 8190
- Closs, G.L.¹ Rabinow, B.E.²

98
- 0342514907
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 6565
- Eisenthal, K.B.¹ Turro, N.J.² Aikawa, M.³ Butcher J.A., Jr.⁴ DuPuy, C.⁵ Hefferon, G.⁶ Hetherington, W.⁷ Korenowski, G.M.⁸ McAuliffe, M.J.⁹

99
- 0000332401
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 1868
- Sitzmann, E.V.¹ Langan, J.² Eisenthal, K.B.³

100
- 0000818370
- (1984) Chem. Phys. Lett. , vol.110 , pp. 521
- Langan, J.G.¹ Sitzmann, E.V.² Eisenthal, K.B.³

101
- 0001433908
- (1985) Tetrahedron , vol.41 , pp. 1543
- Eisenthal, K.B.¹ Turro, N.J.² Sitzmann, E.V.³ Gould, I.R.⁴ Hefferon, G.⁵ Langan, J.⁶ Cha, Y.⁷

102
- 0000839788
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 966
- Sugiyama, M.H.¹ Celebi, S.² Platz, M.S.³

103
- 84986947118
- (1992) J. Phys. Org. Chem. , vol.5 , pp. 123
- Adamasu, A.S.¹ Platz, M.S.²

104
- 0001197151
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 7011
- Garcia-Garibay, M.A.¹

105
- 0027742309
- (1993) Tetrahedron Lett. , vol.34 , pp. 8415
- Garcia-Garibay, M.A.¹

106
- 0031562045
- (1997) Tetrahedron Lett. , vol.38 , pp. 949
- Motschiedler, K.R.¹ Toscano, J.P.² Garcia-Garibay, M.A.³

107
- 0001888334
- (1995) Bull. Korean Chem. Soc. , vol.16 , pp. 47
- Sung, D.D.¹ Lim, G.T.² Kim, M.S.³ Park, D.K.⁴

108
- 84962432297
- note

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.