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Volumn 72, Issue 4, 2007, Pages 1285-1293

Kinetics of the reactions of [p-nitrophenoxy(phenyl)carbene] pentacarbonylchromium(0) with aryloxide ions, hydroxide ion, and water in aqueous acetonitrile. Concerted or stepwise?

(4) Bernasconi, Claude F a Michoff, Martin E Zoloff a De Rossi, Rita H b Granados, Alejandro M b

a UNIVERSITY OF CALIFORNIA (United States)

b UNIVERSIDAD DE CÓRDOBA (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL OXIDE IONS; NUCLEOPHILIC ATTACK; STRUCTURE-REACTIVITY RELATIONSHIPS;

ACETONITRILE; ALCOHOLS; IONS; PH EFFECTS; REACTION KINETICS; SUBSTITUTION REACTIONS;

NITROGEN COMPOUNDS;

[4 NITROPHENOXY(PHENYL)CARBENE]PENTACARBONYLCHROMIUM; ACETONITRILE; CARBENOID; CARBONYL DERIVATIVE; CHROMIUM DERIVATIVE; HYDROXIDE; OXIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; HYDROLYSIS; ORGANIC CHEMISTRY; PKA; SUBSTITUTION REACTION;

EID: 33846996408 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo062138r Document Type: Article

Times cited : (17)

References (84)

1
- 0003818422
- Verlag Chemie: Deerfield Beach, FL
- Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissl, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Deerfield Beach, FL, 1983.
- (1983) Transition Metal Carbene Complexes
- Dötz, K.H.¹ Fischer, H.² Hofmann, P.³ Kreissl, F.R.⁴ Schubert, U.⁵ Weiss, K.⁶

2
- 31744444770
- (a) Aumann, R.; Hinterding, P.; Krüger, C.; Goddard, R. J. Organomet. Chem. 1993, 459, 145.
- (1993) J. Organomet. Chem , vol.459 , pp. 145
- Aumann, R.¹ Hinterding, P.² Krüger, C.³ Goddard, R.⁴

3
- 0030892426
- (b) Bernasconi, C. F.; Flores, F. X.; Kittredge, K. W. J. Am. Chem. Soc. 1997, 119, 2103.
- (1997) J. Am. Chem. Soc , vol.119 , pp. 2103
- Bernasconi, C.F.¹ Flores, F.X.² Kittredge, K.W.³

4
- 0034694743
- (c) Bernasconi, C. F.; Perez, G. S. J. Am. Chem. Soc. 2000, 122, 12441.
- (2000) J. Am. Chem. Soc , vol.122 , pp. 12441
- Bernasconi, C.F.¹ Perez, G.S.²

5
- 33846987406
- (d) Zoloff Michofi, M. E.; de Rossi, R. H.; Granados, A. M. J. Org. Chem. 2006, 71, 2305.
- (2006) J. Org. Chem , vol.71 , pp. 2305
- Zoloff Michofi, M.E.¹ de Rossi, R.H.² Granados, A.M.³

6
- 2342444387
- (e) Bernasconi, C. F.; Bhattacharya, S. Organometallics 2004, 23, 1722.
- (2004) Organometallics , vol.23 , pp. 1722
- Bernasconi, C.F.¹ Bhattacharya, S.²

7
- 0001664076
- (a) Bernasconi, C. F.; Flores, F. X.; Gandler, J. R.; Leyes, A. E. Organometallics 1994, 13, 2186.
- (1994) Organometallics , vol.13 , pp. 2186
- Bernasconi, C.F.¹ Flores, F.X.² Gandler, J.R.³ Leyes, A.E.⁴

8
- 0040520482
- (b) Bernasconi, C. F.; García-Río, L. J. Am. Chem. Soc. 2000, 122, 3821.
- (2000) J. Am. Chem. Soc , vol.122 , pp. 3821
- Bernasconi, C.F.¹ García-Río, L.²

9
- 0001171175
- (a) Klabunde, U.; Fischer, E. O. J. Am. Chem. Soc. 1967, 89, 7141.
- (1967) J. Am. Chem. Soc , vol.89 , pp. 7141
- Klabunde, U.¹ Fischer, E.O.²

10
- 37049113895
- (b) Connor, J. A.; Fischer, E. O. J. Chem. Soc. A 1969, 578.
- (1969) J. Chem. Soc. A , pp. 578
- Connor, J.A.¹ Fischer, E.O.²

11
- 84962400493
- (c) Fischer, E. O.; Kollmeier, H.-J. Chem. Ber. 1971, 104, 1339.
- (1971) Chem. Ber , vol.104 , pp. 1339
- Fischer, E.O.¹ Kollmeier, H.-J.²

12
- 84984257496
- (d) Fischer, E. O.; Leupold, M. Chem. Ber. 1972, 105, 599.
- (1972) Chem. Ber , vol.105 , pp. 599
- Fischer, E.O.¹ Leupold, M.²

13
- 0001685168
- (e) Fischer, E. O.; Heckl, B.; Werner, H. J. Organomet. Chem. 1971, 28, 359.
- (1971) J. Organomet. Chem , vol.28 , pp. 359
- Fischer, E.O.¹ Heckl, B.² Werner, H.³

14
- 0001203290
- (f) Bernasconi, C. F.; Stronach, M. W. J. Am. Chem. Soc: 1993, 115, 1341.
- (1993) J. Am. Chem. Soc , vol.115 , pp. 1341
- Bernasconi, C.F.¹ Stronach, M.W.²

15
- 0034617205
- (g) Bernasconi, C. F.; Whitesell, C.; Johnson, R. A. Tetrahedron 2000, 56, 4917.
- (2000) Tetrahedron , vol.56 , pp. 4917
- Bernasconi, C.F.¹ Whitesell, C.² Johnson, R.A.³

16
- 0037451073
- (h) Bernasconi, C. F.; Bhattacharya, S. Organometallics 2003, 22, 426, 1310.
- (2003) Organometallics , vol.22 , Issue.426 , pp. 1310
- Bernasconi, C.F.¹ Bhattacharya, S.²

17
- 5144227219
- (i) Ali, M.; Maiti, D. J. Organomet. Chem. 2004, 680, 3520.
- (2004) J. Organomet. Chem , vol.680 , pp. 3520
- Ali, M.¹ Maiti, D.²

18
- 23844481774
- (j) Ali, M.; Dan, A.; Ray, A.; Ghosh, K. Inorg. Chem. 2005, 44, 5866.
- (2005) Inorg. Chem , vol.44 , pp. 5866
- Ali, M.¹ Dan, A.² Ray, A.³ Ghosh, K.⁴

19
- 26444491024
- (k) Ali, M.; Gangopadhyay, S.; Mijanuddin, Md. J. Organomet. Chem. 2005, 690, 4878.
- (2005) J. Organomet. Chem , vol.690 , pp. 4878
- Ali, M.¹ Gangopadhyay, S.² Mijanuddin, M.³

20
- 84984205196
- (a) Fischer, E. O.; Leupold, M.; Kreiter, C. G.; Müller, J. Chem. Ber. 1972, 105, 150.
- (1972) J. Chem. Ber , vol.105 , pp. 150
- Fischer, E.O.¹ Leupold, M.² Kreiter, C.G.³ Müller⁴

21
- 0001617656
- (b) Lam, C. T.; Senoff, C. V.; Ward, J. E. H. J. Organomet. Chem. 1974, 70, 273.
- (1974) J. Organomet. Chem , vol.70 , pp. 273
- Lam, C.T.¹ Senoff, C.V.² Ward, J.E.H.³

22
- 0012304038
- (c) Aumann, R.; Schröder, J. Chem. Ber. 1990, 123, 2053.
- (1990) Chem. Ber , vol.123 , pp. 2053
- Aumann, R.¹ Schröder, J.²

23
- 0033591883
- (d) Bernasconi, C. F.; Kittredge, K. W.; Flores, F. X. J. Am. Chem. Soc. 1999, 121, 6630.
- (1999) J. Am. Chem. Soc , vol.121 , pp. 6630
- Bernasconi, C.F.¹ Kittredge, K.W.² Flores, F.X.³

24
- 84982067046
- (a) Fischer, E. O.; Riedmüller, S. Chem. Ber. 1976, 109, 3358.
- (1976) Chem. Ber , vol.109 , pp. 3358
- Fischer, E.O.¹ Riedmüller, S.²

25
- 0000723813
- (b) Fischer, E. O.; Held, W.; Kreissl, F. R. Chem. Ber. 1977, 110, 3842.
- (1977) Chem. Ber , vol.110 , pp. 3842
- Fischer, E.O.¹ Held, W.² Kreissl, F.R.³

26
- 0012272161
- (c) Burkhardt, T. J.; Casey, C. P. J. Am. Chem. Soc. 1973, 95, 5833.
- (1973) J. Am. Chem. Soc , vol.95 , pp. 5833
- Burkhardt, T.J.¹ Casey, C.P.²

27
- 0000277502
- (d) Fischer, E. O.; Held, F. R.; Kreissl, F. R.; Frank, A.; Hattner, G. Chem. Ber. 1977, 110, 656.
- (1977) Chem. Ber , vol.110 , pp. 656
- Fischer, E.O.¹ Held, F.R.² Kreissl, F.R.³ Frank, A.⁴ Hattner, G.⁵

28
- 33847088717
- (e) Casey, C. P.; Burkhardt, T. J.; Bunnell, C. A; Calabrese, J. C. J. Am. Chem. Soc. 1977, 99, 2127.
- (1977) J. Am. Chem. Soc , vol.99 , pp. 2127
- Casey, C.P.¹ Burkhardt, T.J.² Bunnell, C.A.³ Calabrese, J.C.⁴

29
- 11044226055
- (f) Bernasconi, C. F.; Ali, M. Organometallics 2004, 23, 6134.
- (2004) Organometallics , vol.23 , pp. 6134
- Bernasconi, C.F.¹ Ali, M.²

30
- 27144490336
- (g) Ali, M. Ind. J. Chem. A 2005, 44A, 1817.
- (2005) Ind. J. Chem. A , vol.44 A , pp. 1817
- Ali, M.¹

31
- 84982063543
- (a) Fischer, E. O.; Kreis, G.; Kreissl, F. R.; Kreiter, C. G.; Müller, J. J. Chem. Ber. 1973, 106, 3910.
- (1973) J. Chem. Ber , vol.106 , pp. 3910
- Fischer, E.O.¹ Kreis, G.² Kreissl, F.R.³ Kreiter, C.G.⁴ Müller, J.⁵

32
- 0001382614
- (b) Casey, C. P.; Brunsvold, W. P. Inorg. Chem. 1977, 16, 391.
- (1977) Inorg. Chem , vol.16 , pp. 391
- Casey, C.P.¹ Brunsvold, W.P.²

33
- 0001294293
- (c) Bell, R. A.; Chisholm, M. H.; Couch, D. A.; Rankel, L. A. Inorg. Chem. 1977, 16, 677.
- (1977) Inorg. Chem , vol.16 , pp. 677
- Bell, R.A.¹ Chisholm, M.H.² Couch, D.A.³ Rankel, L.A.⁴

34
- 33846288279
- (a) Bernasconi, C. F. Chem. Soc. Rev. 1997, 26, 299.
- (1997) Chem. Soc. Rev , vol.26 , pp. 299
- Bernasconi, C.F.¹

35
- 0141905306
- (b) Bernasconi, C. F. Adv. Phys. Org. Chem. 2002, 37, 137.
- (2002) Adv. Phys. Org. Chem , vol.37 , pp. 137
- Bernasconi, C.F.¹

36
- 0013422958
- (a) Bender, M. L. Chem. Rev. 1966, 60, 53.
- (1966) Chem. Rev , vol.60 , pp. 53
- Bender, M.L.¹

37
- 0001329652
- (b) Jencks, W. P. Chem. Rev. 1972, 72, 705.
- (1972) Chem. Rev , vol.72 , pp. 705
- Jencks, W.P.¹

38
- 0000374270
- (a) Capon, B.; Ghosh, A. K.; Grieve, D. M. A. Acc. Chem. Res. 1981, 14, 306.
- (1981) Acc. Chem. Res , vol.14 , pp. 306
- Capon, B.¹ Ghosh, A.K.² Grieve, D.M.A.³

39
- 33845550196
- (b) McClelland, R. A.; Sandry, L. Acc. Chem. Res. 1983, 16, 394.
- (1983) Acc. Chem. Res , vol.16 , pp. 394
- McClelland, R.A.¹ Sandry, L.²

40
- 0033996380
- Bernasconi, C. F.; Ali, M.; Lu, F. J. Am. Chem. Soc: 2000, 122, 1352.
- (2000) J. Am. Chem. Soc , vol.122 , pp. 1352
- Bernasconi, C.F.¹ Ali, M.² Lu, F.³

41
- 0035817662
- (b) Bernasconi, C. F.; Ali, M. Organometallics 2001, 20, 3383.
- (2001) Organometallics , vol.20 , pp. 3383
- Bernasconi, C.F.¹ Ali, M.²

42
- 33845281499
- Ba-Saif, S.; Luthra, A. K.; Williams, A. J. Am. Chem. Soc. 1987, 109, 6362.
- (1987) J. Am. Chem. Soc , vol.109 , pp. 6362
- Ba-Saif, S.¹ Luthra, A.K.² Williams, A.³

43
- 33845183356
- Ba-Saif, S.; Luthra, A. K.; Williams, A. J. Am. Chem. Soc. 1989, 111, 2647.
- (1989) J. Am. Chem. Soc , vol.111 , pp. 2647
- Ba-Saif, S.¹ Luthra, A.K.² Williams, A.³

44
- 0001488907
- (a) Stefanidis, D.; Cho, S.; Dhe-Pagenon, S.; Jencks, W. P. J. Am. Chem. Soc. 1993, 115, 1650.
- (1993) J. Am. Chem. Soc , vol.115 , pp. 1650
- Stefanidis, D.¹ Cho, S.² Dhe-Pagenon, S.³ Jencks, W.P.⁴

45
- 0000144108
- (b) Hengge, A. C.; Hess, R. A. J. Am. Chem. Soc. 1994, 116, 11256.
- (1994) J. Am. Chem. Soc , vol.116 , pp. 11256
- Hengge, A.C.¹ Hess, R.A.²

46
- 0033529728
- (c) Fernandez, M. A.; de Rossi, R. M. J. Org. Chem. 1999, 64, 6000.
- (1999) J. Org. Chem , vol.64 , pp. 6000
- Fernandez, M.A.¹ de Rossi, R.M.²

47
- 33846979328
- Even though this view has been challenged,16 it has been upheld in subsequent studies.14
- 14

48
- 33845184610
- (a) Buncel, E.; Um, I. H.; Hoz, S. J. Am. Chem. Soc. 1989, 111, 971.
- (1989) J. Am. Chem. Soc , vol.111 , pp. 971
- Buncel, E.¹ Um, I.H.² Hoz, S.³

49
- 0001352132
- (b) Kwon, D.-S.; Lee, G.-J.; Um, I. H. Bull. Korean Chem. Soc. 1990, 11, 262.
- (1990) Bull. Korean Chem. Soc , vol.11 , pp. 262
- Kwon, D.-S.¹ Lee, G.-J.² Um, I.H.³

50
- 33847000410
- See the Supporting Information paragraph at the end of this paper
- See the Supporting Information paragraph at the end of this paper.

51
- 0033591883
- Bernasconi, C. F.; Kittredge, K. W.; Flores, F. X. J. Am. Chem. Soc. 1999, 121, 6630.
- (1999) J. Am. Chem. Soc , vol.121 , pp. 6630
- Bernasconi, C.F.¹ Kittredge, K.W.² Flores, F.X.³

52
- 0033573029
- Bernasconi, C. F.; Ali, M. J. Am. Chem. Soc. 1999, 121, 11384.
- (1999) J. Am. Chem. Soc , vol.121 , pp. 11384
- Bernasconi, C.F.¹ Ali, M.²

53
- 0000476090
- Jencks, W. P.; Haber, M. T.; Herschlag, D.; Nazaretian, K. L. J. Am. Chem. Soc. 1986, 108, 479.
- (1986) J. Am. Chem. Soc , vol.108 , pp. 479
- Jencks, W.P.¹ Haber, M.T.² Herschlag, D.³ Nazaretian, K.L.⁴

54
- 37049076070
- Richard, J. P. J. Chem. Commun. 1987, 1768.
- (1987) J. Chem. Commun , pp. 1768
- Richard, J.P.¹

55
- 7844221156
- McClelland, R. A.; Kanagasabapathy, V. M.; Banait, N. S.; Steenken, S. J. Am. Chem. Soc. 1992, 114, 1816.
- (1992) J. Am. Chem. Soc , vol.114 , pp. 1816
- McClelland, R.A.¹ Kanagasabapathy, V.M.² Banait, N.S.³ Steenken, S.⁴

56
- 0037423974
- (a) Terrier, F.; Le Guével, E.; Chatrousse, A. P.; Moutier, G.; Buncel, E. Chem. Comm. 2003, 600.
- (2003) Chem. Comm , pp. 600
- Terrier, F.¹ Le Guével, E.² Chatrousse, A.P.³ Moutier, G.⁴ Buncel, E.⁵

57
- 33751009096
- Terrier, F.; Rodriguez-Dafonte, P.; Le, Guével, E.; Montiers, G. Org. Biomol. Chem. 2006, 4, 4352.
- (b) Terrier, F.; Rodriguez-Dafonte, P.; Le, Guével, E.; Montiers, G. Org. Biomol. Chem. 2006, 4, 4352.

58
- 0001225213
- Andraos, J.; Kresge, A. J. J. Am. Chem. Soc. 1992, 114, 5643.
- (1992) J. Am. Chem. Soc , vol.114 , pp. 5643
- Andraos, J.¹ Kresge, A.J.²

59
- 33846971836
- However, two chlorine substituents in ortho positions lead to a strong steric effect.12
- 12

60
- 33846958261
- 2 would also show a slight increase due to an enhanced electronic push by the electron pairs on the aryloxy group oxygen.
- 2 would also show a slight increase due to an enhanced electronic push by the electron pairs on the aryloxy group oxygen.

61
- 33846966990
- The σP values for 4-CF3, 4-CN, 4-CHO, and 4-NO2 are 0.54, 0.66, 0.42, and 0.78, respectively, while the σP- values are 0.56, 0.99, 0.98, and 1.28, respectively.28 Hence, the Δσ, σP, σP values for 4-CF3, 4-CN, 4-CHO, and 4-NO 2 are 0.02, 0.33, 0.56, and 0.49, respectively. σR values, another measure of π-acceptor strength, yield the same qualitative order: 0.09 (4-CF3, 0.18 (4-CN, 0.23 (4-CHO, and 0.16 (4-NO 2).28
- 28

62
- 4243664295
- Hansch, C.; Leo. A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
- (1991) Chem. Rev , vol.91 , pp. 165
- Hansch, C.¹ Leo, A.² Taft, R.W.³

63
- 33846992150
- The Marcus intrinsic barrier of a reaction is the barrier in the absence of a thermodynamic driving force, i.e, when ΔG°, 0. 30
- 30

64
- 33947306589
- Marcus, R. A. J. Phys. Chem. 1968, 72, 891.
- (1968) J. Phys. Chem , vol.72 , pp. 891
- Marcus, R.A.¹

65
- 33845283144
- Bernasconi, C. F. Acc. Chem. Res. 1987, 20, 301.
- (1987) Acc. Chem. Res , vol.20 , pp. 301
- Bernasconi, C.F.¹

66
- 0008305649
- (b) Bernasconi, C. F. Adv. Phys. Org. Chem. 1992, 27, 119.
- (1992) Adv. Phys. Org. Chem , vol.27 , pp. 119
- Bernasconi, C.F.¹

67
- 0002767827
- (c) Bernasconi, C. F. Acc. Chem. Res. 1992, 25, 9.
- (1992) Acc. Chem. Res , vol.25 , pp. 9
- Bernasconi, C.F.¹

68
- 33847086871
- (a) Jencks, W. P. Acc. Chem. Res. 1980, 13, 161.
- (1980) Acc. Chem. Res , vol.13 , pp. 161
- Jencks, W.P.¹

69
- 37049099359
- (b) Jencks W. P. Chem. Soc. Rev. 1981, 10, 345.
- (1981) Chem. Soc. Rev , vol.10 , pp. 345
- Jencks, W.P.¹

70
- 0000743849
- Gandler, J. R.; Bernasconi, C. F. Organometallics 1989, 8, 2282.
- (1989) Organometallics , vol.8 , pp. 2282
- Gandler, J.R.¹ Bernasconi, C.F.²

71
- 0030567338
- Amyes, T. L.; Richard, J. P. J. Am. Chem. Soc. 1996, 118, 3129.
- (1996) J. Am. Chem. Soc , vol.118 , pp. 3129
- Amyes, T.L.¹ Richard, J.P.²

72
- 0001203290
- Bernasconi, C. F.; Stronach, M. W. J. Am. Chem. Soc 1993, 115, 1341.
- (1993) J. Am. Chem. Soc , vol.115 , pp. 1341
- Bernasconi, C.F.¹ Stronach, M.W.²

73
- 33847800139
- Jencks, W. P. Acc. Chem. Res. 1976, 9, 425.
- (1976) Acc. Chem. Res , vol.9 , pp. 425
- Jencks, W.P.¹

74
- 5244245983
- Hammond, G. S. J. Am. Chem. Soc. 1955, 77, 334.
- (1955) J. Am. Chem. Soc , vol.77 , pp. 334
- Hammond, G.S.¹

75
- 0003558028
- Wiley: New York
- Leffler, J. E.; Grunwald, E. Rates and Equilibria of Organic Reactions; Wiley: New York, 1963.
- (1963) Rates and Equilibria of Organic Reactions
- Leffler, J.E.¹ Grunwald, E.²

76
- 33847002566
- 40
- 40

77
- 33745454255
- Bernasconi, C. F.; Brown, S. D.; Ali, M.; Rappoport, Z.; Yamataka H.; Salim, H. J. Org. Chem. 2006, 71, 4795.
- (2006) J. Org. Chem , vol.71 , pp. 4795
- Bernasconi, C.F.¹ Brown, S.D.² Ali, M.³ Rappoport, Z.⁴ Yamataka, H.⁵ Salim, H.⁶

78
- 33846958611
- 28
- 28

79
- 33846941779
- Other factors such as the smaller electron withdrawing inductive effect of the MeS group compared to MeO and PhO groups contribute to differences in the k1OH values.2c
- 2c

80
- 33947477676
- Jencks, W. P.; Gilchrist, M. J. Am. Chem. Soc. 1962, 84, 2910.
- (1962) J. Am. Chem. Soc , vol.84 , pp. 2910
- Jencks, W.P.¹ Gilchrist, M.²

81
- 33847088916
- Hupe, D. J.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 451.
- (1977) J. Am. Chem. Soc , vol.99 , pp. 451
- Hupe, D.J.¹ Jencks, W.P.²

82
- 0033518048
- Pulley, S. R.; Sen. S.; Vogorushin, A.; Swanson, E. Org. Lett. 1999, 1, 1721.
- (1999) Org. Lett , vol.1 , pp. 1721
- Pulley, S.R.¹ Sen, S.² Vogorushin, A.³ Swanson, E.⁴

83
- 0004055425
- 3rd ed, Pergamon Press: New York
- Perrin, D. D.; Armarego, L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: New York, 1989.
- (1989) Purification of Laboratory Chemicals
- Perrin, D.D.¹ Armarego, L.F.²

84
- 0000447481
- Allen, A. D.; Tidwell, T. T. J. Am. Chem. Soc 1987, 109, 2774.
- (1987) J. Am. Chem. Soc , vol.109 , pp. 2774
- Allen, A.D.¹ Tidwell, T.T.²

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