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Author:

Zhao, L.-J. (Zhao, L.-J..) (Scholars:赵丽娇) | Zhong, R.-G. (Zhong, R.-G..) (Scholars:钟儒刚) | She, Y.-B. (She, Y.-B..) | Dai, Q.-H. (Dai, Q.-H..)

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Scopus PKU CSCD

Abstract:

The non-α-position metabolites of nitrosamines play an important role in chemical carcinogenesis. Ab initio computations are carried out to study the reactivity of β- and γ-position metabolites of methylakylnitrosamines. Taking N-methyl-N-nitroso-2-(sulfate)ethylamine(I), N-methyl-N-nitroso-2-(phosphate)ethylamine(II), N-methyl-N-nitroso-2- (glucuronate)ethylamine(III), N-methyl-N-nitroso-3-(sulfate)-propylamine (IV), N-methyl-N-nitroso-3-(phosphate)propylamine(V), and N-methyl-N-nitroso-3- (glucuronate)propylamine (VI) as models, we investigate their reactivity with the anchimeric assistant process of the N-nitroso groups. Full geometric structure optimization has been done for all reactants, intermediates and transition states. The activation energies, vibrational frequencies and IRC are also obtained. All computations are performed at RHF/6-31G(d) and MP2/6-31G(d) levels. The results show that the reactivity of the sulfates (I and IV) are obviously higher than those of the phosphates (II and V) and the glucuronates (III and VI). And these data indicate that the anchimeric assistance is much more efficient when the leaving group is on the β-carbon than on the γ-carbon.

Keyword:

Ab initio; Alkylnitrosamines; Anchimeric assistance; Non-α-metabolites; Reactivity

Author Community:

  • [ 1 ] [Zhao, L.-J.]College of Life Science and Bioengineering, Beijing University of Technology, Beijing 100022, China
  • [ 2 ] [Zhong, R.-G.]College of Life Science and Bioengineering, Beijing University of Technology, Beijing 100022, China
  • [ 3 ] [She, Y.-B.]College of Life Science and Bioengineering, Beijing University of Technology, Beijing 100022, China
  • [ 4 ] [Dai, Q.-H.]College of Life Science and Bioengineering, Beijing University of Technology, Beijing 100022, China

Reprint Author's Address:

  • 钟儒刚

    [Zhong, R.-G.]College of Life Science and Bioengineering, Beijing University of Technology, Beijing 100022, China

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Source :

Acta Physico - Chimica Sinica

ISSN: 1000-6818

Year: 2005

Issue: 8

Volume: 21

Page: 883-887

1 0 . 9 0 0

JCR@2022

ESI Discipline: CHEMISTRY;

JCR Journal Grade:4

Cited Count:

WoS CC Cited Count: 0

SCOPUS Cited Count:

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 3

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