Unraveling the impact of hydrogen bonding and C-H ... π(CN) interactions in crystal engineering of cyclic aminobenzonitriles: A combined X-ray crystallographic and computational investigation ...

被引：8

作者：

Zaib, Sumera ^{[1
]}

Ibrar, Aliya ^{[2
]}

Khan, Imtiaz ^{[3
]}

Gomila, Rosa M. ^{[4
]}

Tariq, Muhammad Umair ^{[5
]}

Simpson, Jim ^{[6
]}

McAdam, Christopher John ^{[6
]}

Alrbyawi, Hamad ^{[7
]}

Pashameah, Rami Adel ^{[8
]}

Alzahrani, Eman ^{[9
]}

Farouk, Abd-ElAziem ^{[10
]}

Frontera, Antonio ^{[4
]}

机构：

[1] Univ Cent Punjab, Fac Sci & Technol, Dept Basic & Appl Chem, Lahore 54590, Pakistan

[2] Univ Haripur, Fac Phys & Appl Sci, Dept Chem, KPK 22620, Pakistan

[3] Univ Manchester, Manchester Inst Biotechnol, Dept Chem, 131 Princess St, Manchester M17DN, England

[4] Univ Illes Balears, Dept Quim, Crta Valldemossa Km 7-5 Baleares, Palma De Mallorca 07122, Spain

[5] Chartered Univ, Forman Christian Coll, Fac Nat Sci, Dept Chem, Lahore 54600, Pakistan

[6] Univ Otago, Dept Chem, POB 56, Dunedin 9054, New Zealand

[7] Taibah Univ, Coll Pharm, Pharmaceut & Pharmaceut Technol Dept, Medina 42353, Saudi Arabia

[8] Umm Al Qura Univ, Fac Appl Sci, Dept Chem, Mecca 24230, Saudi Arabia

[9] Taif Univ, Coll Sci, Dept Chem, POB 11099, Taif 21944, Saudi Arabia

[10] Taif Univ, Coll Sci, Dept Biotechnol, POB 11099, Taif 21944, Saudi Arabia

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2023年 / 1273卷

关键词：

Nitrile; Noncovalent interactions; Hydrogen bonding; Aromatic contacts; DFT calculations; QTAIM analysis; NONCOVALENT INTERACTIONS; PI INTERACTIONS; NITRILE; REACTIVITY; COORDINATION; HIGHLIGHTS; MECHANISMS; CYSTEINE; SCAFFOLD; DENSITY;

D O I：

10.1016/j.molstruc.2022.134387

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The essential role of organic crystals in drug development represents a significant research area and remains enduringly topical within the pharmaceutical industry. In the present study, four cyclic aminobenzonitriles 3a-d were prepared through the nucleophilic aromatic substitution reaction of 4-fluorobenzonitrile with various cyclic amines. The synthesized compounds were obtained in moderate to good yields and structurally characterized by FTIR, NMR spectroscopy, mass spectrometry and X-ray crystallography. The crystal packing of these compounds predominantly involves the use of hydro-gen bonding interactions (C-H...N, C-H...S, C-H...O) and aromatic contacts (C-H...pi(ring & CN), pi...pi) to govern the complex structural topology. These noncovalent interactions were further evaluated by molecular electrostatic potential (MEP) surface analysis and DFT energy calculations confirming the importance of pi-stacking and CH...pi interactions, either involving the arene or the pi-system of the cyano groups. These interactions have been further characterized using the QTAIM/NCIplot computational tool. (c) 2022 Elsevier B.V. All rights reserved.

引用

页数：9

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