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

共 49 条

[41] Bidimensional self-assembling of [HgII(RPhNNNPhR')2] (R = acetyl, R' = F) through metal-η4-arene π-interactions and non classical C-H••• O bonding:: Synthesis and X-ray characterization of a bis diaryl asymmetric-substituted triazenide complex polymer of Hg(II)
Hörner, M
de Oliveira, GM
Giglio, VF
Visentin, LDC
Broch, F
Beck, J
INORGANICA CHIMICA ACTA, 2006, 359 (07) : 2309 - 2313
[42] CRYSTAL-STRUCTURE OF CD5(CN)10(H2O)4.4C6H11OH STUDIED BY X-RAY-DIFFRACTION AND SOLID-STATE CD-113 NMR - A NEW TYPE OF CRISTOBALITE-LIKE FRAMEWORK HOST WITH A SITE INTERACTING WITH CYCLOHEXANOL BY HYDROGEN-BONDING
NISHIKIORI, S
RATCLIFFE, CI
RIPMEESTER, JA
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (22) : 8590 - 8595
[43] The nature of solid-state N-H•••O/O-H•••N tautomeric competition in resonant systems.: Intramolecular proton transfer in low-barrier hydrogen bonds formed by the •••O=C-C=N-NH•••⇆HO-C=C-N=N••• ketohydrazone-azoenol system.: A variable-temperature X-ray crystallographic and DFT computational study
Gilli, P
Bertolasi, V
Pretto, L
Lycka, A
Gilli, G
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (45) : 13554 - 13567
[44] THE X-RAY CRYSTAL-STRUCTURES OF [MO(C=CPH)(PH2PCH2CH2PPH2)(ETA-C7H7)] AND [MO(C=CPH)(PH2PCH2CH2PPH2)(ETA-C7H7)] [BF4] (C7H7 = CYCLOHEPTATRIENYL) - AN INVESTIGATION OF METAL-ALKYNYL BONDING
BEDDOES, RL
BITCON, C
WHITELEY, MW
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 402 (01) : 85 - 96
[45] Supramolecular Self-Assembling of [HgII(RC6H4NNNC6H4R)2Py] [R = EtOC(O)] through Reciprocal Metal-η2-arene π-Interactions and Non Classical C-H•••O Bonding: Synthesis and X-ray Characterization of a Bis Diaryl Symmetric-substituted Triazenide Complex Polymer of Hg(II)
Hoerner, Manfredo
de Oliveira, Gelson M.
Villis, Paulo C. M.
Visentin, Lorenzo do C.
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2008, 19 (08) : 1641 - 1645
[46] Polymeric bidimensional self-assembling of [HgII(RC6H4NNNC6H4R)2PY] (R= m-acetyl) through metal-η2,η2-arene π-interactions and non classical C-H•••O bonding:: Synthesis and X-ray characterization of a bis diaryl symmetric-substituted triazenide complex of Hg(II)
Hörner, M
de Oliveira, GM
Koehler, EG
do CantoVisentin, L
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (06) : 1311 - 1314
[47] Impact of Aromatic Ring Count on the Ability to Participate in Attractive Interactions. Crystal Structure (X-ray) and Solid State Computational (DFT/QTAIM/RDS/Hirshfeld-surfaces) Study of 1,4-di(2-phenyl-1H-imidazol-4-yl)benzene. A Potential Nanotechnology Intrinsic Component
Latosinska, Jolanta Natalia
Latosinska, Magdalena
Maurin, Jan Krzysztof
Kazimierczuk, Zygmunt
CRYSTAL GROWTH & DESIGN, 2015, 15 (11) : 5464 - 5475
[48] RING HYDROGEN C-H ACTIVATION IN (CP-STAR-2)LNCH(SIME3)2 (LN=Y, LA, CE) - X-RAY CRYSTAL-STRUCTURES OF [CP-STAR-3(MU-3-ETA-5,ETA-1,ETA-1-C5ME3(CH2)2)CE2]2 AND (CP-STAR-2)CECH2C6H5
BOOIJ, M
MEETSMA, A
TEUBEN, JH
ORGANOMETALLICS, 1991, 10 (09) : 3246 - 3252
[49] Second sphere coordination complex via hydrogen bonding: Synthesis, spectroscopic studies of [(C6H5)3RP][trans-Co(NH3)2(NO2)4] where R = benzyl, phenyl or ethyl and X-ray crystal structure of [(C6H5)4P][trans-Co(NH3)2(NO2)4]
Sharma, Raj Pal
Singh, Ajnesh
Venugopalan, Paloth
JOURNAL OF MOLECULAR STRUCTURE, 2008, 888 (1-3) : 107 - 112

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