Theoretical Study of Pnicogen Bonding Interactions between PH2X and Five-membered Heterocycles

doi:10.6023/A13030332

Acta Chimica Sinica ›› 2013, Vol. 71 ›› Issue (08): 1175-1182.DOI: 10.6023/A13030332 Previous Articles Next Articles

Article

PH₂X与五元杂环体系磷键相互作用的理论研究

许惠英^a, 王维^b, 邹建卫^c

a 浙江树人大学生物与环境工程学院杭州 310015;
b 镇海环境监测站宁波 315200;
c 浙江大学宁波理工学院宁波 315104

投稿日期:2013-03-25 发布日期:2013-05-06
通讯作者: 许惠英, E-mail: xuhy65@163.com E-mail:xuhy65@163.com
基金资助:
项目受国家自然科学基金(No. 21272211)和浙江省自然科学基金(No. LY12B07013)资助.

Theoretical Study of Pnicogen Bonding Interactions between PH₂X and Five-membered Heterocycles

Xu Huiying^a, Wang Wei^b, Zou Jianwei^c

a College of Biology & Environment Engineering, Zhejiang Shuren University, Hangzhou 310015;
b Zhenhai Environmental Monitoring Station, Ningbo 315200;
c Ningbo Institute of Technology, Zhejiang University, Ningbo 315104

Received:2013-03-25 Published:2013-05-06
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21272211) and the Zhejiang Provincial Natural Science Foundation (No. LY12B07013).

1. Theoretical Study of Pnicogen Bonding Interactions between PH₂X and Five-membered Heterocycles.PDF(294KB)

Abstract

Intermolecular interactions between PH₂X (X=H, F, Cl, Br) and five-member heterocyclic compounds (pyrrole, furan, thiophene) were calculated by using MP2/aug-cc-pVDZ quantum chemical method, and the interaction energies were corrected with BSSE (basis set superposition error) by complete counterpoise correction method. On the basis of MP2/aug-cc-pVDZ optimized geometries, the second-order perturbation stabilization energies (ΔE²) and AIM properties were calculated using the NBO (natural bond orbital) program in Gaussian 03 and AIM 2000 program, respectively. In order to further understand this type of interaction, graphical analyses for representative systems were performed using the reduced density gradient (RDG) color-filled isosurface map and the electronic density difference map. It has been showed that the P—H…π hydrogen bonding interaction is formed between PH₃ and three five-member heterocyclic compounds, and the pnicogen bonding interactions between PH₂X (X=F, Cl, Br) and five-member heterocyclic compounds. There exist two types of pnicogen bonding interactions (π- and n-types) in these complexes, and the stabilities of the π-type pnicogen bonded complexes are stronger than those of the n-type ones. Moreover, the interaction energies have been found to correlate closely with the angle between P—X vector and the direction vector of P atom to the heterocyclic centroid. For comparison, intermolecular interactions between PCl₃ and the three kinds of heterocyclic compounds were also studied. It has been showed that three positive electrostatic potential areas (or “σ-hole”) are presented at phosphorus atom end along the Cl—P bond in PCl₃ molecule, so the complexes with multi-pnicogen-bonding can be formed between PCl₃ and the heterocyclic compounds. Through atom in molecule (AIM) analysis, it has been disclosed that the nature of all the pnicogen bonding interactions belongs to the closed-shell electrostatic interactions, and the stabilities of the complexes are correlated positively with the electron densities in the bond critical points (BCPs). RDG graphical analyses are performed to visualize the positions and strengths of the pnicogen bonding. DDF analyses are also done, and indicating that electron density is reduced at phosphorus atom end and increased around the P—X axis and five-member heterocyclic molecule because of the pnicogen bonding inte-raction, thus the underlying rearrangement of the electron densities is intuitively reflected.

Key words: pnicogen bonding, NBO, AIM, RDG isosurface map, electronic density difference

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Xu Huiying, Wang Wei, Zou Jianwei. Theoretical Study of Pnicogen Bonding Interactions between PH₂X and Five-membered Heterocycles[J]. Acta Chimica Sinica, 2013, 71(08): 1175-1182.

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PH₂X与五元杂环体系磷键相互作用的理论研究

Theoretical Study of Pnicogen Bonding Interactions between PH₂X and Five-membered Heterocycles

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PH2X与五元杂环体系磷键相互作用的理论研究