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Unstable, metastable, or stable halogen bonding interaction involving negatively charged donors? A statistical and computational chemistry study.

The noncovalent halogen bonding could be attributed to the attraction between the positively charged sigma -hole and a nucleophile. Quantum mechanics (QM) calculation indicated that the negatively charged organohalogens have no positively charged sigma -hole on their molecular surface, leading to a... Full description

Journal Title: The journal of physical chemistry. B December 11, 2014, Vol.118(49), pp.14223-14233
Main Author: Yang, Zhuo
Other Authors: Xu, Zhijian , Liu, Yingtao , Wang, Jinan , Shi, Jiye , Chen, Kaixian , Zhu, Weiliang
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: E-ISSN: 1520-5207 ; DOI: 10.1021/jp506291v
Link: http://search.proquest.com/docview/1637556242/?pq-origsite=primo
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title: Unstable, metastable, or stable halogen bonding interaction involving negatively charged donors? A statistical and computational chemistry study.
format: Article
creator:
  • Yang, Zhuo
  • Xu, Zhijian
  • Liu, Yingtao
  • Wang, Jinan
  • Shi, Jiye
  • Chen, Kaixian
  • Zhu, Weiliang
subjects:
  • Halogens–Chemistry
  • Hydrocarbons, Halogenated–Chemistry
  • Models, Molecular–Chemistry
  • Molecular Dynamics Simulation–Chemistry
  • Quantum Theory–Chemistry
  • Thermodynamics–Chemistry
  • Halogens
  • Hydrocarbons, Halogenated
ispartof: The journal of physical chemistry. B, December 11, 2014, Vol.118(49), pp.14223-14233
description: The noncovalent halogen bonding could be attributed to the attraction between the positively charged sigma -hole and a nucleophile. Quantum mechanics (QM) calculation indicated that the negatively charged organohalogens have no positively charged sigma -hole on their molecular surface, leading to a postulation of repulsion between negatively charged organohalogens and nucleophiles in vacuum. However, PDB survey revealed that 24% of the ligands with halogen bonding geometry could be negatively charged. Moreover, 36% of ionizable drugs in CMC (Comprehensive Medicinal Chemistry) are possibly negatively charged at pH 7.0. QM energy scan showed that the negatively charged halogen bonding is probably metastable in vacuum. However, the QM calculated bonding energy turned negative in various solvents, suggesting that halogen bonding with negatively charged donors should be stable in reality. Indeed, QM/MM calculation on three crystal structures with negatively charged ligands revealed that the negatively charged halogen bonding was stable. Hence, we concluded that halogen bonding with negatively charged donors is unstable or metastable in vacuum but stable in protein environment, and possesses similar geometric and energetic characteristics as conventional halogen bonding. Therefore, negatively charged organohalogens are still effective halogen bonding donors for medicinal chemistry and other applications.
language: eng
source:
identifier: E-ISSN: 1520-5207 ; DOI: 10.1021/jp506291v
fulltext: fulltext
issn:
  • 15205207
  • 1520-5207
url: Link


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titleUnstable, metastable, or stable halogen bonding interaction involving negatively charged donors? A statistical and computational chemistry study.
creatorYang, Zhuo ; Xu, Zhijian ; Liu, Yingtao ; Wang, Jinan ; Shi, Jiye ; Chen, Kaixian ; Zhu, Weiliang
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identifierE-ISSN: 1520-5207 ; DOI: 10.1021/jp506291v
subjectHalogens–Chemistry ; Hydrocarbons, Halogenated–Chemistry ; Models, Molecular–Chemistry ; Molecular Dynamics Simulation–Chemistry ; Quantum Theory–Chemistry ; Thermodynamics–Chemistry ; Halogens ; Hydrocarbons, Halogenated
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descriptionThe noncovalent halogen bonding could be attributed to the attraction between the positively charged sigma -hole and a nucleophile. Quantum mechanics (QM) calculation indicated that the negatively charged organohalogens have no positively charged sigma -hole on their molecular surface, leading to a postulation of repulsion between negatively charged organohalogens and nucleophiles in vacuum. However, PDB survey revealed that 24% of the ligands with halogen bonding geometry could be negatively charged. Moreover, 36% of ionizable drugs in CMC (Comprehensive Medicinal Chemistry) are possibly negatively charged at pH 7.0. QM energy scan showed that the negatively charged halogen bonding is probably metastable in vacuum. However, the QM calculated bonding energy turned negative in various solvents, suggesting that halogen bonding with negatively charged donors should be stable in reality. Indeed, QM/MM calculation on three crystal structures with negatively charged ligands revealed that the negatively charged halogen bonding was stable. Hence, we concluded that halogen bonding with negatively charged donors is unstable or metastable in vacuum but stable in protein environment, and possesses similar geometric and energetic characteristics as conventional halogen bonding. Therefore, negatively charged organohalogens are still effective halogen bonding donors for medicinal chemistry and other applications.
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