Crystal Structure of Halogenated N-Methylquinoline-2-Ones: Preparation and Study of Intermolecular Interactions in Crystals

IF 1.2 4区化学 Q4 CHEMISTRY, INORGANIC & NUCLEAR

Journal of Structural Chemistry Pub Date : 2024-04-30 DOI:10.1134/s0022476624030089

F. K. Verkhov, I. Y. Bagryanskaya, V. I. Krasnov, I. K. Shundrina, G. A. Selivanova

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Abstract

A series of novel N-methylquinoline-2-ones with a fluorinated benzene ring (with and without Br atoms) is prepared by the interaction of halogenated quinoline-2-ones with CH₃I in methanol in the presence of KOH. The molecular and crystal structures of these compounds are determined by XRD. It is shown that the main structure-forming interaction in the crystals of these compounds is π-staking, while the main supramolecular motif is formed by the π-stacks of molecules resulting from the expected π–π-interaction between the electron-deficient haloarene species and a more electron-donating pyridinone ring (fluoroarene–fluoroarene interactions are also present). In all cases, the intra-stack molecular packing changes noticeably upon the transition from fluorinated N-methylfluoroquinoline-2-ones to their bromine-containing derivatives: the lateral shift increases, the Br…π interactions appear. The Br atoms form Br…F or Br…Br intermolecular interactions.

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卤代 N-甲基喹啉-2-酮的晶体结构：晶体中分子间相互作用的制备与研究

摘要通过卤化喹啉-2-酮与甲醇中的 CH3I 在 KOH 存在下的相互作用，制备了一系列具有氟化苯环（含 Br 原子和不含 Br 原子）的新型 N-甲基喹啉-2-酮。通过 XRD 确定了这些化合物的分子结构和晶体结构。结果表明，在这些化合物的晶体中，形成结构的主要相互作用是π-staking，而主要的超分子结构则是由分子的π-stack形成的，这种π-stack是缺电子的卤代烯类与更多电子捐赠的吡啶酮环（也存在芴-芴相互作用）之间预期的π-π-相互作用所产生的。在所有情况下，从含氟的 N-甲基氟喹啉-2-酮过渡到其含溴衍生物时，叠层内分子堆积都会发生明显变化：横向移动增加，Br...π 相互作用出现。Br 原子形成 Br...F 或 Br...Br 分子间相互作用。

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来源期刊

Journal of Structural Chemistry 化学-无机化学与核化学

CiteScore

1.60

自引率

12.50%

发文量

142

审稿时长

8.3 months

期刊介绍： Journal is an interdisciplinary publication covering all aspects of structural chemistry, including the theory of molecular structure and chemical bond; the use of physical methods to study the electronic and spatial structure of chemical species; structural features of liquids, solutions, surfaces, supramolecular systems, nano- and solid materials; and the crystal structure of solids.