Matrix model to predict specific optical rotations of acyclic chiral molecules

doi:10.1016/j.tet.2006.12.061

	Matrix model to predict specific optical rotations of acyclic chiral molecules
	Zhu, Hua-Jie ; Ren, Jie ; Pittman, Charles U., Jr.
通讯作者	hjzhu@mail.kib.ac.cn
	2007-03-05
发表期刊	TETRAHEDRON
ISSN	0040-4020
卷号	63 期号:10 页码:2292-2314
摘要	This paper constructs a new matrix model to analyze the relationship of the stereogenic center and its substituents to the specific optical rotation. The variables used as matrix elements include (1) the substituents' comprehensive masses (m), (2) radii (r), (3) symmetries (s), and (4) the electronegativities (chi) of the atoms or groups which are bound to the stereogenic center. Solution of the matrix determinants was postulated to give scalar numbers proportional to the magnitudes of the specific rotations of the molecules being considered. A total of 94 example calculations were performed to predict the relative magnitude and direction of rotation at the sodium D line. Only two calculations failed to predict the correct direction of rotation and this occurred only when their optical rotation values were less than 0.01 degrees. The B3LYP functional at the aug-cc-pVDZ basis set level was also used to compute the optical rotations of the 66 example chiral molecules whose geometries were previously obtained at the B3LYP/6-31G(d) level. The expected successful predictions for these acydic molecules' optical rotation values did not appear. Overall, the matrix model is one approach to understand the optical rotation. (c) 2006 Elsevier Ltd. All rights reserved.
关键词	Matrix Determinant Optical Rotation B3lyp
学科领域	Chemistry, Organic
DOI	10.1016/j.tet.2006.12.061
收录类别	SCI
语种	英语
WOS记录号	WOS:000244536500022
引用统计
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/2969
专题	植物化学与西部植物资源持续利用国家重点实验室
作者单位	1.Chinese Acad Sci, Kunming Inst Bot, Organ Synth & Nat Prod Lab, Kunming 650204, Yunnan, Peoples R China 2.Mississippi State Univ, Dept Chem, Mississippi State, MS 39762 USA
推荐引用方式 GB/T 7714	Zhu, Hua-Jie,Ren, Jie,Pittman, Charles U., Jr.. Matrix model to predict specific optical rotations of acyclic chiral molecules[J]. TETRAHEDRON,2007,63(10):2292-2314.
APA	Zhu, Hua-Jie,Ren, Jie,&Pittman, Charles U., Jr..(2007).Matrix model to predict specific optical rotations of acyclic chiral molecules.TETRAHEDRON,63(10),2292-2314.
MLA	Zhu, Hua-Jie,et al."Matrix model to predict specific optical rotations of acyclic chiral molecules".TETRAHEDRON 63.10(2007):2292-2314.

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