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Cis/Trans Energetics in Epoxide Thiirane Aziridine and Phosphirane Containing Cyclopentanols: Effects of Intramolecular OH⋯O S N and P Contacts

机译：含环戊醇的环氧化物硫杂环丁烷氮丙啶和磷杂环戊烷中的顺式/反式能量学：分子内OH⋯OSN和P接触的影响

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A recent computational analysis of the stabilizing intramolecular OH⋯O contact in 1,2-dialkyl-2,3-epoxycyclopentanol diastereomers has been extended to thiiriane, aziridine and phosphirane analogues. Density functional theory (DFT), second-order Møller-Plesset perturbation theory (MP2) and CCSD(T) coupled-cluster computations with simple methyl and ethyl substituents indicate that electronic energies of the

c i s

isomers are lowered by roughly 3 to 4 kcal mol⁻¹ when the OH group of these cyclopentanol systems forms an intramolecular contact with the O, S, N or P atom on the adjacent carbon. The results also suggest that S and P can participate in these stabilizing intramolecular interactions as effectively as O and N in constrained molecular environments. The stabilizing intramolecular OH⋯O, OH⋯S, OH⋯N and OH⋯P contacts also increase the covalent OH bond length and significantly decrease the OH stretching vibrational frequency in every system with shifts typically on the order of −41 cm⁻¹.

机译：最近对1，2-二烷基-2，3-环氧环戊醇非对映异构体中稳定的分子内OH ＝ O接触的计算分析已扩展到噻吩，氮丙啶和膦烷类似物上。具有简单甲基和乙基取代基的密度泛函理论（DFT），二阶Møller-Plesset微扰理论（MP2）和CCSD（T）耦合簇计算表明，

cis <当这些环戊醇系统的OH基团与O形成分子内接触时，/ mi>异构体降低约3至4 kcal mol-1 。相邻碳原子上的S，N或P原子。结果还表明，在受限制的分子环境中，S和P可以像O和N一样有效地参与这些稳定的分子内相互作用。稳定的分子内OH⋯O，OH⋯S，OH⋯N和OH⋯P接触也增加了共价OH键的长度并显着降低了每个系统中OH拉伸振动频率，其位移通常约为-41 cm -1 。

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期刊名称 Molecules
作者
Ben E. Smith; Jeremy M. Carr; Gregory S. Tschumper;
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作者单位

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年(卷),期 2019(24),14
年度 2019
页码 2523
总页数 12
原文格式 PDF
正文语种
中图分类分子生物学;
关键词
intramolecular hydrogen bonding semipinacol rearrangement vibrational frequencies density functional theory (DFT) coupled-cluster theory;

机译：分子内氢键;频哪醇重排;振动频率;密度泛函理论（DFT）;耦合簇理论;

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专利

1. Modern valence-bond description of bonding in strained three-membered rings: cyclopropane, aziridine, ethene oxide, phosphirane and thiirane [J] . peter B. Karadakov, Joseph Gerratt, David L. Cooper, Journal of Molecular Structure. Theochem: Applications of Theoretical Chemistry to Organic, Inorganic and Biological Problems . 1995,第1a3期

机译：应变三元环中键的现代价键描述：环丙烷，氮丙啶，环氧乙烷，膦烷和硫杂环丁烷
2. Model Calculations about the Influence of Protic Environments on the Alkylation Step of Epoxide,Aziridine,and Thiirane Based Cysteine Protease Inhibitors [J] . Holger Helten, Tanja Schirmeister, Bernd Engels The journal of physical chemistry, A. Molecules, spectroscopy, kinetics, environment, & general theory . 2004,第38期

机译：质子环境对环氧化物，氮丙啶和硫杂环丁烷半胱氨酸蛋白酶抑制剂烷基化步骤影响的模型计算
3. Inter- and intramolecular pi-stacking interactions in cis-bis{1-(9-anthracene)}phosphirane complexes of platinum(II) [J] . Yang F., Fanwick PE., Kubiak CP. Inorganic Chemistry: A Research Journal that Includes Bioinorganic, Catalytic, Organometallic, Solid-State, and Synthetic Chemistry and Reaction Dynamics . 2002,第18期

机译：铂（II）的顺-双{1-（9-蒽）}膦烷配合物中的分子间和分子内pi堆积相互作用
4. Effects of Cis and Trans Unsaturation on the Barotropic and Thermotropic Phase Behavior of Phospholipid Bilayers [C] . S. Kaneshina, H. Matsuki, M. Kusube, International Conference on High Pressure Bioscience and Biotechnology . 2003

机译：CIS和反式不饱和对磷脂双层的波奇磷和热致相行为的影响
5. Intramoleculer Hydrogen Bonding in Epoxide, Thiirane, Aziridine and Phosphirane Containing Cyclopentanols [D] . Smith, Ben E. 2019

机译：含环氧化物，硫烷，氮丙酮和含有环戊醇的磷脂中的肠内氢键合
6. Catalytic activities of mammalian epoxide hydrolases with cis and trans fatty acid epoxides relevant to skin barrier function [O] . Haruto Yamanashi, William E. Boeglin, Christophe Morisseau, 2018

机译：与皮肤屏障功能有关的顺式和反式脂肪酸环氧化物对哺乳动物环氧化物水解酶的催化活性
7. Application of photoelectron spectroscopy to intramolecularly hydrogen-bonded systems. Part III. The photoelectron spectra of cis and trans 2-substituted cyclopentanols and cis and trans 2-substituted cyclohexanols [O] . R. S. Brown 1976

机译：光电子光谱法在分子内氢键体系中的应用。第三部分。 CIS和反式2取代的环戊醇和CIS和反式2取代的环己醇的光电子能谱
8. Intramolecular Energy Transfer and cis-trans Isomerization in HONO [R] . Guan, Y., Lynch, G. C., Thompson, D. L. 1987

机译：HONO中的分子内能量转移和顺反异构化

Cis/Trans Energetics in Epoxide Thiirane Aziridine and Phosphirane Containing Cyclopentanols: Effects of Intramolecular OH⋯O S N and P Contacts

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