THE EFFECT OF PARA-SUBSTITUENTS ON THE CONFORMATIONAL BEHAVIOR OF 2,2-DIARYL-1,3-OXAZINE-4,6-DIONES - EVIDENCE FROM A CRYSTAL-STRUCTURE DETERMINATION

被引：3

作者：

SATO, M ^{[1
]}

NAGASHIMA, S ^{[1
]}

MURAKAMI, M ^{[1
]}

KANEKO, C ^{[1
]}

FURUYA, T ^{[1
]}

机构：

[1] YAMANOUCHI PHARMACEUT CO LTD,TSUKUBA RES LABS,TSUKUBA,IBARAKI 305,JAPAN

来源：

TETRAHEDRON | 1993年 / 49卷 / 30期

关键词：

D O I：

10.1016/S0040-4020(01)81826-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The crystal structure of 2,3-bis(4-methoxyphenyl)-2-(4-nitrophenyl)-1,3-oxazine-4,6-dione (9) was elucidated by X-ray structure analysis. This analysis has revealed two interesting characteristics: 1) The molecule is in a boat conformation with C(2) and C(5) pointing upward with angles of 41.9-degrees and 26.0-degrees, respectively and 2) The 4-nitrophenyl group takes a quasi-axial conformation. The second characteristic can be interpreted in terms of stabilizing interaction between the lone pairs on N(3) and/or O(1) and the sigma*-orbital on the axial C(2)-aryl bond. The similar interaction of the lone pairs to pi-orbitals of C(4 and 6)=O is also considered to account for the first characteristic.

引用

页码：6575 / 6580

页数：6

共 10 条

[1] INVESTIGATION OF AZINES AND AZOLES .62. STRUCTURE OF THE 2-ARYL-1,3-OXAZINE-4,6-DIONES
ZAKHS, VE
YAKOVLEV, IP
SMORYGO, NA
GINDIN, VA
IVIN, BA
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1987, (03): : 386 - 394
[2] INVESTIGATIONS OF AZOLES AND AZINES .75. THE STRUCTURE OF 2-ARYL-1,3-OXAZINE-4,6-DIONES IN THE GAS-PHASE
ZAKHS, VE
VIKTOROVSKII, IV
IVIN, BA
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1990, (04): : 552 - 556
[3] THE EFFECT OF PARA-SUBSTITUENTS ON THE CONFORMATIONAL BEHAVIOR OF 2-ARYL-1,3-DITHIANES
KOHLER, H
TSCHIERSKE, C
ZASCHKE, H
KLEINPETER, E
TETRAHEDRON, 1990, 46 (12) : 4241 - 4246
[4] Effect of Remote Aryl Substituents on the Conformational Equilibria of 2,2-Diaryl-1,3-dioxanes: Importance of Electrostatic Interactions
Bailey, William F.
Lambert, Kyle M.
Wiberg, Kenneth B.
Mercado, Brandon Q.
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (08): : 4108 - 4115
[5] CONFORMATIONAL BEHAVIOR OF DIMETHYL-2,2'-DIPYRIDYL LIGANDS - CRYSTAL-STRUCTURE OF 4,6-DIMETHYL-2,2'-DIPYRIDYL-DICARBONYLNICKEL(0)
SIELER, J
THAN, NN
BENEDIX, R
DINJUS, E
WALTHER, D
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1985, 522 (03): : 131 - 136
[6] The effect of a para substituent on the conformational preference of 2,2-diphenyl-1,3-dioxanes: Evidence for the anomeric effect from X-ray crystal structure analysis
Uehara, F
Sato, M
Kaneko, C
Kurihara, H
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (05): : 1436 - 1441
[7] The effect of a para substituent on the conformational preference of 2,2-diphenyl-1,3-dioxanes: Evidence for the anomeric effect from X-ray crystal structure analysis
Uehara, Fumiaki
Sato, Masayuki
Kaneko, Chikara
Kurihara, Hiroyuki
Journal of Organic Chemistry, 1999, 64 (2-5): : 1436 - 1441
[8] STUDY OF AZINES AND AZOLES .82. BASE-CATALYZED DIMERIZATION OF 2-ARYL-1,3-OXAZINE-4,6-DIONES - CRYSTALLINE AND MOLECULAR-STRUCTURE OF 6-N-METHOXYBENZOYLAMINO-3-N-METHOXYBENZOYLAMINOCARBONYL-4-HYDROXY-2-PYRANONE
ZAKHS, VE
YAKOVLEV, IP
GINDIN, VA
CHUMAKOV, YM
BIYUSHKIN, VN
MALINOVSKII, TI
IVIN, BA
ZHURNAL ORGANICHESKOI KHIMII, 1992, 28 (12): : 2611 - 2619
[9] 2,2-DIMETHYL-5-(5-R-FURFURYLYDENE-2)-1,3-DIOXANE-4,6-DIONES .3. CRYSTAL AND MOLECULAR-STRUCTURE OF 2,2-DIMETHYL-5-(5-METHYL-2-FURFURYLYDENE)-1,3-DIOXANE-4,6-DIONE
KRAPIVIN, GD
ZAVODNIK, VE
BELSKII, VK
VALTER, NI
KULNEVICH, VG
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1988, (11): : 1453 - 1456
[10] 2,2-DIMETHYL-5-(5-R-FURFURYLIDENE)-1,3-DIOXANE-4,6-DIONES .6. SYNTHESIS, STRUCTURE AND PROPERTIES OF SUBSTITUTED FURYLIMINOPHOSPHORANE AND FURFURYLIDENEPHOSPHORANE - MOLECULAR AND CRYSTAL-STRUCTURE OF N-[5-(2,2-DIMETHYL-4,6-DIOXO-1,3-DIOXAN-5-YLIDEN)METHYLFURYL-2] IMINOTRIPHENYLPHOSPHORANE
KRAPIVIN, GD
VALTER, NI
ZAVODNIK, VE
KAKLYUGINA, TY
KULNEVICH, VG
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1994, (03): : 335 - 344

← 1 →