GEOMETRY CHANGES OF ARYL AMINO-GROUPS RESULTING FROM CHANGES IN ELECTRON WITHDRAWAL - AN ABINITIO MOLECULAR-ORBITAL STUDY

被引：15

作者：

ADAMS, DB

机构：

[1] ICI Wilton Research Centre, Wilton, Middlesbrough, TS6 8JE

[2] University of Sunderland, School of Health Sciences, Galen Building

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1993年 / 03期

关键词：

D O I：

10.1039/p29930000567

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Changes in the geometry of aryl amino groups in aniline, aminopyridines and protonated forms of these molecules have been studied by ab initio 6-31 G* molecular orbital calculations. The pyramidal nature of the amino group in aniline is reduced by increased pi-electron withdrawal by the ring but coplanarity with the ring (sp2 hybridized nitrogen) only results when a very strongly pi-electron withdrawing centre is conjugated with the amino group.

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页码：567 / 571

页数：5

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[1] MNDO CALCULATIONS AND THE NONPLANARITY OF ARYLAMINO GROUPS [J].

ADAMS, DB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (02) :247-248

[2]

Albert, 1984, DETERMINATION IONIZA

[3] PROPERTIES OF ATOMS IN MOLECULES - ELECTROPHILIC AROMATIC-SUBSTITUTION [J].

BADER, RFW ;

CHANG, C .

JOURNAL OF PHYSICAL CHEMISTRY, 1989, 93 (08) :2946-2956

[4] PROPERTIES OF ATOMS IN MOLECULES - ENERGETICS OF ELECTROPHILIC AROMATIC-SUBSTITUTION [J].

BADER, RFW ;

CHANG, C .

JOURNAL OF PHYSICAL CHEMISTRY, 1989, 93 (13) :5095-5107

[5] A MOLECULAR-ORBITAL STUDY OF NITROGEN INVERSION IN ANILINE WITH EXTENSIVE GEOMETRY OPTIMIZATION [J].

BOCK, CW ;

GEORGE, P ;

TRACHTMAN, M .

THEORETICA CHIMICA ACTA, 1986, 69 (03) :235-245

[6] ABINITIO CALCULATION OF AMINE OUT-OF-PLANE ANGLES [J].

BOGGS, JE ;

NIU, ZF .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1985, 6 (01) :46-55

[7] THE ORIGIN OF THE DIFFERENCE IN THE BARRIERS TO INVERSION IN ANILINE AND N-METHYLANILINE [J].

CERVELLATI, R ;

DEGLI ESPOSTI, A ;

LISTER, DG ;

PALMIERI, P .

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 1985, 23 (3-4) :173-177

[8] ATOMIC CHARGES DERIVED FROM ELECTROSTATIC POTENTIALS - A DETAILED STUDY [J].

CHIRLIAN, LE ;

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JOURNAL OF COMPUTATIONAL CHEMISTRY, 1987, 8 (06) :894-905

[9] MICROWAVE-SPECTRA AND STRUCTURE OF AMINE GROUP IN 3-AMINOPYRIDINE AND 4-AMINOPYRIDINE - AB-INITIO MOLECULAR-ORBITAL CALCULATIONS OF STRUCTURE OF AMINE GROUP IN AMINOPYRIDINES [J].

CHRISTEN, D ;

NORBURY, D ;

LISTER, DG ;

PALMIERI, P .

JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS II, 1975, 71 :438-446

[10] REPRESENTATION OF THE MOLECULAR ELECTROSTATIC POTENTIAL BY A NET ATOMIC CHARGE MODEL [J].

COX, SR ;

WILLIAMS, DE .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1981, 2 (03) :304-323

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