Supramolecular architectures of N-acetyl-L-proline monohydrate and N-benzyl-L-proline.

IF 0.8 4区 化学 Acta crystallographica. Section C, Crystal structure communications Pub Date : 2013-11-01 Epub Date: 2013-10-05 DOI:10.1107/S010827011302581X
P Rajalakshmi, N Srinivasan, R V Krishnakumar, Ibrahim Abdul Razak, Mohd Mustaqim Rosli
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引用次数: 5

Abstract

The title compounds, N-acetyl-L-proline monohydrate, C7H11NO3·H2O, (I), and N-benzyl-L-proline, C12H15NO2, (II), crystallize in the monoclinic space group P21 with Z' = 1 and Z' = 2, respectively. The conformation of C(γ) with respect to the carboxylic acid group in (I) is C(γ)-exo or UP pucker, with the pyrrolidine ring twisted, while in (II), it is C(γ)-endo or DOWN, with the pyrrolidine ring assuming an envelope conformation. The crystal packing interactions in (I) are composed of two substructures, one characterized by an R6(6)(24) motif through O-H...O hydrogen bonds and the other by an R4(4)(23) ring through C-H...O interactions. In (II), the crystal packing interactions consist of N-H...O and C-H...O hydrogen bonds. Proline (Pro) exists in its neutral form in (I) and is zwitterionic in (II). This difference in the ionization states of Pro is manifested through the absence of N-H...O and presence of O-H...O interactions in (I), and the presence of N-H...O and absence of O-H...O hydrogen bonds in (II). While C-H...O interactions are present in both (I) and (II), the geometry of the synthons formed by them and their mode of participation in intermolecular interactions is different. Though the title compounds differ significantly in terms of modifications in the Pro skeleton, the differences in their supramolecular structures may also be viewed as a result of the molecular recognition facilitated by the presence of a solvent water molecule in (I) and the zwitterionic state of the amino acid in (II).

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一水合n -乙酰- l-脯氨酸和n -苄基- l-脯氨酸的超分子结构。
标题化合物n -乙酰基- l-脯氨酸一水合物C7H11NO3·H2O (I)和n -苄基- l-脯氨酸C12H15NO2 (II)在单斜空间群P21中分别以Z' = 1和Z' = 2结晶。在(I)中,C(γ)与羧基的构象为C(γ)-外显或UP pucker,吡咯烷环扭曲;而在(II)中,C(γ)-内显或DOWN构象,吡咯烷环呈包络构象。(1)中的晶体填充相互作用由两个子结构组成,其中一个通过O-H…O氢键和另一个由R4(4)(23)环通过C-H…O交互。在(II)中,晶体填充相互作用由N-H…O和碳氢键…O氢键。脯氨酸(Pro)在(I)中以中性形式存在,在(II)中以两性离子形式存在。脯氨酸(Pro)的这种电离状态的差异是通过缺少N-H来表现的。O和O- h的存在…(I)中O相互作用,N-H…O和O- h的缺失…O氢键在(II)中,而C-H…O相互作用存在于(I)和(II)中,它们形成的合子的几何形状和参与分子间相互作用的方式是不同的。虽然标题化合物在Pro骨架上的修饰有很大的不同,但它们的超分子结构的差异也可以看作是(I)中溶剂水分子的存在和(II)中氨基酸的两性离子状态促进了分子识别的结果。
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期刊介绍: Acta Crystallographica Section C: Structural Chemistry is continuing its transition to a journal that publishes exciting science with structural content, in particular, important results relating to the chemical sciences. Section C is the journal of choice for the rapid publication of articles that highlight interesting research facilitated by the determination, calculation or analysis of structures of any type, other than macromolecular structures. Articles that emphasize the science and the outcomes that were enabled by the study are particularly welcomed. Authors are encouraged to include mainstream science in their papers, thereby producing manuscripts that are substantial scientific well-rounded contributions that appeal to a broad community of readers and increase the profile of the authors.
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Equilin. (+-)-Tartaric acid. DL-Proline. DL-Alanine. The Etymology of Chemical Names. Tradition and Convenience vs. Rationality in Chemical Nomenclature. By Alexander Senning. De Gruyter, 2019. Hardcover, Pp. xiv+505. Price EUR 149.95, USD 172.99, GBP 136.50. ISBN 978-3-11-061106-9.
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