CONFORMATIONAL STUDY OF 2,4-DIARYL-3-AZABICYCLO[3.3.1]NONAN-9-ONES AND THEIR 3-METHYL DERIVATIVES BY QUANTUM-MECHANICAL CALCULATIONS, NMR, AND X-RAY CRYSTALLOGRAPHY

被引:11
作者
ARIAS, MS
SMEYERS, YG
FERNANDEZ, MJ
SMEYERS, NJ
GALVEZ, E
FONSECA, I
SANZAPARICIO, J
机构
[1] CSIC, INST ESTRUCTURA MAT, E-28006 MADRID, SPAIN
[2] CSIC, INST ROCASOLANO, UEI CRISTALOGRAFIA, E-28006 MADRID, SPAIN
关键词
D O I
10.1021/jo00088a044
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Some 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones 1 and their N-methyl derivatives 2 have been synthesized and studied by semiempirical quantum mechanical calculations and H-1-NMR spectroscopy (AM1/H-1 tandem) in order to establish their conformational preferences. The crystal structure of 3-methyl-2,4-diphenyl-3-azabicyclo [3. 3.1] nonan-9-one, 2a, has been determined by X-ray diffraction. It is found that compounds 1 present a CC-alpha preferred conformation in the gas phase and in CDCl3 solution, while the CC-beta form is observed in the solid state. This latter conformation, with the N-H bond in the equatorial position (CC-beta), seems to be favored by the formation of intermolecular hydrogen bonds in the crystal. Compounds 2 are practically monoconformational and display a slightly flattened CC conformation with the N-methyl group in the equatorial position (CC-beta).
引用
收藏
页码:2565 / 2569
页数:5
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