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Steric Effect Determines the Formation of Lactam–Lactam Dimers or Amide C═O···NH (Lactam) Chain Motifs in N-Phenyl-2-hydroxynicotinanilides
Crystal Growth & Design ( IF 3.8 ) Pub Date : 2020-04-29 , DOI: 10.1021/acs.cgd.0c00023
H. Liu 1 , X. Yang 1 , S. Cao 1 , F. Yu 1 , S. Long 1 , J. Chen 2 , M. Zhang 2 , S. Parkin 3 , T. Li 4 , Z. Yang 5
Affiliation  

A series of N-phenyl-2-hydroxynicotinanilides (PHNAs) have been synthesized, and their crystal structures have been investigated. The identity of these compounds is revealed to be the tautomer of PHNAs, i.e., 2-oxo-1,2-dihydropyridine-3-carboxylic acid phenylamides, compounds with both amide and lactam functionalities. Among these compounds, those with no or negligible steric hindrance take a near planar conformation and form lactam–lactam dimers, not the widely observed amide NH···O═C hydrogen bond chains, while those with steric hindrance take a twisted conformation and form an amide NH···O═C (lactam) hydrogen bond. A succinct theoretic study combining conformational analysis and molecular electrostatic potential surfaces (MEPS) survey provided a reasonable explanation of the formation of these two different hydrogen bond motifs.

中文翻译:

立体效应决定了N-苯基-2-羟基烟酰胺中内酰胺-内酰胺二聚体或酰胺C═O··NH(内酰胺)链基团的形成

N系列已经合成了-苯基-2-羟基烟酰胺(PHNA),并且已经研究了它们的晶体结构。揭示这些化合物的身份是PHNA的互变异构体,即具有酰胺和内酰胺功能的2-OXO-1,2-二氢吡啶-3-羧酸苯基酰胺。在这些化合物中,没有或没有位阻的化合物呈近似平面构象,形成内酰胺-内酰胺二聚体,而不是广为观察的酰胺NH···O═C氢键链,而有位阻的化合物呈扭曲构象和形式。酰胺NH···O═C(内酰胺)氢键。结合构象分析和分子静电势面(MEPS)调查的简洁理论研究为这两个不同的氢键基序的形成提供了合理的解释。
更新日期:2020-07-01
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