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Journal of the American Chemical Society

Volumn 124, Issue 35, 2002, Pages 10552-10562

Site of protonation of nicotine and nornicotine in the gas phase: Pyridine or pyrrolidine nitrogen?

(9) Graton, Jérôme a Berthelot, Michel a Gal, Jean François c Girard, Sandrine b Laurence, Christian a Lebreton, Jacques b Le Questel, Jean Yves a Maria, Pierre Charles c Nauš, Petr d

a UNIVERSITÉ DE NANTES (France)

b Centre National de la Recherche Scientifique (France)

c UNIVERSITÉ CÔTE D'AZUR (France)

d CHARLES UNIVERSITY (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINITY; NITROGEN; POLARIZATION; SUBSTITUTION REACTIONS; WATER;

NICOTINE;

CHEMICAL ANALYSIS;

NICOTINE; NORNICOTINE; PYRIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; DRUG DERIVATIVE; NITROGEN; PROTON;

AB INITIO CALCULATION; ARTICLE; ELECTRON TRANSPORT; GEOMETRY; HYDROGEN BOND; MOLECULAR MODEL; POLARIZATION; PROTON TRANSPORT; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; BINDING SITE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; ELECTRICITY; GAS; THERMODYNAMICS;

BINDING SITES; ELECTROSTATICS; GASES; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NICOTINE; NITROGEN; PROTONS; THERMODYNAMICS;

EID: 0037019545 PISSN: 00027863 EISSN: None Source Type: Journal
DOI: 10.1021/ja017770a Document Type: Article

Times cited : (83)

References (87)

1
- 0014934202
- (1970) Nature , vol.228 , pp. 917
- Beers, W.H.¹ Reich, E.²

2
- 0025778840
- (1991) Science , vol.253 , pp. 872
- Sussman, J.L.¹ Harel, M.² Frolow, F.³ Oefner, C.⁴ Goldman, A.⁵ Toker, L.⁶ Silman, I.⁷

3
- 0027368530
- (1993) Proc. Natl. Acad. Sci. U.S.A. , vol.90 , pp. 9031
- Harel, M.¹ Shalk, I.² Ehret-Sabatier, L.³ Bouet, F.⁴ Goeldner, M.⁵ Nirth, C.⁶ Axelsen, P.H.⁷ Silman, I.⁸ Sussman, J.L.⁹

4
- 0033960085
- (2000) J. Phannacol. Exp. Ther. , vol.292 , pp. 461
- Lloyd, G.K.¹ Williams, M.²

5
- 0031450275
- (1997) J. Med. Chem. , vol.40 , pp. 4169
- Holladay, M.W.¹ Dart, M.J.² Lynch, J.K.³

6
- 0033577991
- (1999) J. Med. Chem. , vol.42 , pp. 2227
- Latli, B.¹ D'Amour, K.² Casida, J.E.³

7
- 0034213308
- (2000) J. Med. Chem. , vol.43 , pp. 2217
- Nielsen, S.F.¹ Nielsen, E.O.² Olsen, G.M.³ Liljefors, T.⁴ Peters, D.⁵

8
- 0034597576
- (2000) J. Med. Chem. , vol.43 , pp. 4045
- Mullen, G.¹ Napier, J.² Balestra, M.³ De Cory, T.⁴ Hale, G.⁵ Macor, J.⁶ Mack, R.⁷ Loch J. III⁸ Wu, E.⁹ Kover, A.¹⁰ Verhoest, P.¹¹ Sampognaro, A.¹² Phillips, E.¹³ Zhu, Y.¹⁴ Murray, R.¹⁵ Griffith, R.¹⁶ Blosser, J.¹⁷ Gurley, D.¹⁸ Machulskis, A.¹⁹ Zongrone, J.²⁰ Rosen, A.²¹ Gordon, J.²² more..

9
- 0022485091
- (1986) J. Med. Chem. , vol.29 , pp. 899
- Sheridan, R.P.¹ Nilakantan, R.² Scott Dixon, J.³ Venkataraghavan, R.⁴

10
- 0025675821
- (1990) Science , vol.250 , pp. 1558
- Dougherty, D.A.¹ Stauffer, D.A.²

11
- 12044260020
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 9907
- Kearney, P.C.¹ Mizoue, L.S.² Kumpf, R.A.³ Forman, J.E.⁴ McCurdy, A.⁵ Dougherty, D.A.⁶

12
- 84980110403
- (1962) Br. J. Pharmacol. Chemother. , vol.18 , pp. 543
- Barlow, R.B.¹ Hamilton, J.T.²

13
- 84986550271
- (1974) Prog. Phys. Org. Chem. , vol.11 , pp. 263
- Jones, F.M.¹ Arnett, E.M.²

14
- 0010224834
- (1980) Bull. Chem. Soc. Jpn. , vol.53 , pp. 2055
- Sawada, M.¹ Ichihara, M.² Yukawa, Y.³ Nakachi, T.⁴ Tsuno, Y.⁵

15
- 0003569330
- Chapman and Hall: London
- (1981) a prediction for organic acids and bases
- Perrin, D.D.¹ Dempsey, B.² Serjeant, E.P.³

16
- 49649150838
- (1971) Pest. Biochem. Phys. , vol.1 , pp. 151
- Fujita, T.¹ Nakajima, M.² Soeda, Y.³ Yamamoto, I.⁴

17
- 0001616854
- (1986) Acta Crystallogr., Sect. C , vol.42 , pp. 853
- Barlow, R.B.¹ Howard, J.A.K.² Johnson, A.³

18
- 0000387712
- (1971) Acta Crystallogr., Sect. B , vol.27 , pp. 1123
- Kim, H.S.¹ Jeffrey, G.A.²

19
- 0003678746
- Academic Press: New York; Chapter 5
- (1985) The Proton: Applications to Organic Chemistry
- Stewart, R.¹

20
- 33748627179
- (1996) J. Phys. Chem. , vol.100 , pp. 1536
- Bagno, A.¹ Scorrano, G.²

21
- 0033802166
- (2000) Acc. Chem. Res. , vol.33 , pp. 609
- Bagno, A.¹ Scorrano, G.²

22
- 0035811443
- (2001) J. Phys. Chem. A , vol.105 , pp. 6537
- Bagno, A.¹ Terrier, F.²

23
- 0000079318
- (1995) Bull. Soc. Chim. Fr. , vol.132 , pp. 394
- Maria, P.-C.¹ Leito, I.² Gal, J.-F.³ Exner, O.⁴ Decouzon, M.⁵

24
- 0001147920
- (1996) Struct. Chem. , vol.7 , pp. 321
- Castano, O.¹ Notario, R.² Hori, K.³ Abboud, J.-L.M.⁴

25
- 0033741004
- (2000) J. Phys. Chem. A , vol.104 , pp. 5122
- Lamsabhi, M.¹ Alcami, M.² Mó, O.³ Bouab, W.⁴ Essefar, M.⁵ Abboud, J.-L.M.⁶ Yanez, M.⁷

26
- 0032561797
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 13224
- Notario, R.¹ Abboud, J.-L.M.² Cativiela, C.³ Garcia, J.Y.⁴ Herreros, M.⁵ Homan, H.⁶ Mayoral, J.A.⁷ Salvatella, L.⁸

27
- 33751499794
- (1991) J. Org. Chem. , vol.56 , pp. 4490
- Berthelot, M.¹ Decouzon, M.² Gal, J.-F.³ Laurence, C.⁴ Le Questel, J.-Y.⁵ Maria, P.-C.⁶ Tortajada, J.⁷

28
- 0033975523
- (2000) J. Org. Chem. , vol.65 , pp. 742
- Elmore, D.E.¹ Dougherty, D.A.²

29
- 84983035977
- (1987) Prog. Phys. Org. Chem. , vol.16 , pp. 1
- Taft, R.W.¹ Topsom, R.D.²

30
- 0001073909
- (1988) J. Org. Chem. , vol.53 , pp. 1137
- Abboud, J.-L.M.¹ Catalan, J.² Elguero, J.³ Taft, R.W.⁴

31
- 0003956918
- Mc-Graw Hill: New York
- (1970) Physical Organic Chemistry, 2nd ed.
- Hammett, L.P.¹

32
- 84983048216
- (1987) Prog. Phys. Org. Chem. , vol.16 , pp. 125
- Topsom, R.D.¹

33
- 0000216589
- (1997) Mol. Struct. (THEOCHEM) , vol.397 , pp. 231
- Exner, O.¹ Ingr, M.² Eársky, P.J.³

34
- 0142119983
- (1998) Phys. Org. Chem. , vol.11 , pp. 485
- Čársky, P.¹ Nauš, P.² Exner, O.J.³

35
- 4243664295
- (1991) Chem. Rev. , vol.91 , pp. 165
- Hansch, C.¹ Leo, A.² Taft, R.W.³

36
- 0020445076
- (1982) J. Org. Chem. , vol.47 , pp. 4165
- Jacob P. III¹

37
- 0031623267
- (1998) Mass Spectrom. Rev. , vol.17 , pp. 1
- Marshall, A.G.¹ Hendrickson, C.L.² Jackson, G.S.³

38
- 0034716207
- (2000) Int. J. Mass Spectrom. , vol.200 , pp. 187
- McMahon, T.B.¹

39
- 0034910836
- (2001) J. Mass Spectrom. , vol.36 , pp. 699
- Gal, J.-F.¹ Maria, P.-C.² Raczinska, E.D.³

40
- 0020718996
- (1983) Vacuum , vol.33 , pp. 149
- Bartmess, J.E.¹ Georgiadis, R.²

41
- 0345720252
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 8533
- Miller, K.J.¹

42
- 0001963013
- (1993) J. Am. Soc. Mass Spectrom. , vol.4 , pp. 54
- Decouzon, M.¹ Gal, J.-F.² Gayraud, J.³ Maria, P.-C.⁴ Vaglio, G.-A.⁵ Volpe, P.⁶

43
- 0032366914
- (1998) J. Phys. Chem. Ref. Data , vol.27 , pp. 413
- Hunter, E.P.¹ Lias, S.G.²

44
- 0011487788
- (1991) J. Org. Chem. , vol.56 , pp. 179
- Chen, L.-Z.¹ Flammang, R.² Maquestiau, A.³ Taft, R.W.⁴ Catalan, J.⁵ Cabildo, P.⁶ Claramunt, E.M.⁷ Elguero, J.⁸

45
- 33947485697
- (1964) J. Med. Chem. , vol.7 , pp. 395
- Free, S.M.¹ Wilson, J.W.²

47
- 33845281510
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 7968
- Bader, R.F.W.¹ Carroll, M.T.² Cheeseman, J.R.³ Chang, C.⁴

48
- 0000189651
- (1993) J. Chem. Phys. , vol.98 , pp. 5648
- Becke, A.D.¹

49
- 77956779984
- (1992) J. Chem. Phys. , vol.96 , pp. 2155
- Becke, A.D.¹

50
- 84986467031
- (1995) J. Comput. Chem. , vol.16 , pp. 263
- Llamas-Saiz, A.L.¹ Foces-Foces, C.² Mó, O.³ Yáñez, M.⁴ Elguero, J.⁵

51
- 0346175395
- (1994) J. Phys. Chem. , vol.98 , pp. 3681
- Florián, J.¹ Johnson, B.G.²

52
- 4243490976
- (1995) Chem. Phys. Lett. , vol.246 , pp. 10
- Bauschlicher, C.W.¹

53
- 0001149067
- (1997) J. Phys. Chem. A , vol.101 , pp. 1927
- Martell, J.M.¹ Goddard, J.D.² Eriksson, L.A.³

54
- 0001042394
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 12366
- Cui, Q.¹ Musaev, D.² Svensson, M.³ Seiber, S.⁴ Morokuma, K.⁵

55
- 0000993764
- (1995) J. Phys. Chem. , vol.99 , pp. 5922
- Ricca, A.¹ Bauschlicher, C.W.²

56
- 0344791553
- (1991) Chem. Rev. , vol.91 , pp. 651
- Ziegler, T.¹

57
- 0000666964
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 4885
- Smith, B.J.¹ Radom, L.²

58
- 4243447021
- (1994) Chem. Phys. Lett. , vol.231 , pp. 345
- Smith, B.J.¹ Radom, L.²

59
- 33748534534
- (1996) J. Phys. Chem. , vol.100 , pp. 10490
- González, A.I.¹ Mó, O.² Yáñez, M.³ León, E.⁴ Tortajada, J.⁵ Morizur, J.-P.⁶ Leito, I.⁷ Maria, P.-C.⁸ Gal, J.-F.⁹

60
- 0000756158
- (1996) New J. Chem. , vol.20 , pp. 1011
- Amekraz, B.¹ Tortajada, J.² Morizur, J.-P.³ González, A.I.⁴ Mó, O.⁵ Yáñez, M.⁶ Leito, I.⁷ Maria, P.-C.⁸ Gal, J.-F.⁹

61
- 0003422992
- Gaussian, Inc.: Pittsburgh, PA
- (1995) Exploring Chemistry with Electronic Structure Methods, 2nd ed.
- Foresman, J.B.¹ Frisch, A.²

62
- 0004270702
- McGraw-Hill: New York; Chapter 22
- (1988) Physical Chemistry, 3rd ed.
- Levine, I.N.¹

63
- 33845549905
- (1983) Acc. Chem. Res. , vol.16 , pp. 292
- Topsom, R.D.¹

64
- 0021177680
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 7
- Marriott, S.¹ Topsom, R.D.²

65
- 37049096539
- (1985) J. Chem. Soc., Perkin Trans. 2 , pp. 1045
- Marriott, S.¹ Topsom, R.D.²

66
- 0000738372
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 1711
- Hehre, W.J.¹ Pau, C.F.² Headley, A.D.³ Taft, R.W.⁴

67
- 33845373869
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 7381
- Kahn, S.D.¹ Pau, C.² Overman, L.E.³ Hehre, W.J.⁴

68
- 0017318432
- (1976) J. Org. Chem. , vol.41 , pp. 1585
- Whidby, J.F.¹ Seeman, J.I.²

69
- 0017854578
- (1978) J. Am. Chem. Soc. , vol.100 , pp. 246
- Pitner, T.P.¹ Edwards, W.B.² Bassfield, R.L.³ Whidby, J.F.⁴

70
- 0010221750
- (1984) Heterocycles , vol.22 , pp. 165
- Seeman, J.I.¹

71
- 0010221628
- (1986) J. Mol. Spectrosc. , vol.117 , pp. 184
- Caminati, W.¹ Scappini, F.²

72
- 33845379057
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 2309
- Pfafferott, G.¹ Oberhammer, H.² Boggs, J.E.³

73
- 0002373841
- (1998) J. Mol. Spectrosc. , vol.191 , pp. 45
- Caminati, W.¹ Dell'Erba, A.² Maccaferri, G.³ Favero, P.G.⁴

74
- 33947327887
- (1968) J. Am. Chem. Soc. , vol.90 , pp. 5636
- Brauman, J.¹ Blair, L.K.²

75
- 0029071709
- (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 991
- Elliott, R.L.¹ Ryther, K.B.² Anderson, D.J.³ Raszkiewicz, J.L.⁴ Campbell, J.E.⁵ Sullivan, J.P.⁶ Gawey, D.S.⁷

76
- 0032748797
- (1999) Eur. J. Med. Chem. , vol.34 , pp. 31
- Dukat, M.¹ Dowd, M.² Damaj, M.I.³ Martin, B.⁴ El-Zahabi, M.A.⁵ Glennon, R.A.⁶

78
- 33748546968
- (1996) J. Phys. Chem. , vol.100 , pp. 7384
- Rowland, R.S.¹ Taylor, R.²

79
- 0004263533
- Cambridge University Press: Cambridge, UK
- (1973) The Hammett Equation , pp. 101
- Johnson, C.D.¹

80
- 0000919359
- (1992) J. Chem. Res. S , pp. 110
- Murray, J.¹ Politzer, P.²

81
- 33751499871
- (1991) J. Org. Chem. , vol.56 , pp. 6715
- Murray, J.S.¹ Politzer, P.²

82
- 0001576358
- (1995) Can. J. Chem. , vol.73 , pp. 483
- Hagelin, H.¹ Murray, J.S.² Brinck, T.³ Berthelot, M.⁴ Politzer, P.⁵

83
- 0034163661
- (2000) Phys. Chem. Chem. Phys. , vol.2 , pp. 973
- Platts, J.A.¹

84
- 0034718647
- (2000) J. Mol. Struct. , vol.552 , pp. 17
- Gu, Y.¹ Kar, T.² Scheiner, S.³

85
- 2142751785
- (2000) Chem. Br. , vol.36 , pp. 20

86
- 0002228660
- (2000) Chem. Eng. News , vol.78 , Issue.MARCH 27 , pp. 23
- Brennan, M.B.¹

87
- 0004141833
- Masson: Paris
- (1997) Nicotine et troubles neuropsychiatriques
- Aubin, H.J.¹

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