Spectroscopic and theoretical investigation of solvent effect on N-H•••O, N-H•••N and N-H•••π interactions in complexes of N-monosubstituted benzamides

被引：4

作者：

Kordic, Branko ^{[1
]}

Dimic, Dusan ^{[2
]}

Despotovic, Vesna ^{[1
]}

Jovic, Branislav ^{[1
]}

机构：

[1] Univ Novi Sad, Fac Sci, Dept Chem Biochem & Environm Protect, Trg D Obradovica 3, Novi Sad 21000, Serbia

[2] Univ Belgrade, Fac Phys Chem, Studentski Trg 12-16,118, Belgrade 11158, Serbia

来源：

JOURNAL OF MOLECULAR LIQUIDS | 2024年 / 399卷

关键词：

N -monosubstituted benzamides; Hydrogen bond; DFT; FT; -IR; Molecular descriptors; Solvent effect; AB-INITIO; FT-IR; HYDROGEN; DERIVATIVES; INHIBITORS; CATECHOLAMINES; POLYMERASE; DOCKING; ANALOGS; DESIGN;

D O I：

10.1016/j.molliq.2024.124472

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：

In this research, experimental and theoretical spectral analysis of N-monosubstituted benzamides was performed by mid-infrared spectroscopy and density functional theory. The MIR spectroscopic characteristics for N-H center dot center dot center dot O, N-H center dot center dot center dot N and N-H center dot center dot center dot pi hydrogen-bonded complexes and also the equilibrium constants for 1:1 complex formation are given. The structures of selected N-substituted benzamides (as proton donors), benzene, acetonitrile, and tetrahydrofuran (as proton acceptors), as well as their complexes, were optimised at the M06-2X/6-311++G (d,p) level of theory. The solvent effect on hydrogen-bonded complexes and the correlations between the equilibrium constants and molecular descriptors of N-monosubstituted benzamides were also investigated using a principal component analysis.

引用

页数：9

共 47 条

[21] Ultrasonic and DFT studies of aliphatic amine - Cyclic ether interactions in n-hexane solvent at 303.15K [J].

Hussain, S. G. Mohamed ;

Kumar, R. ;

Ali, M. Mohamed Naseer ;

Shanmugapriyan, B. ;

Kannappan, V .

JOURNAL OF MOLECULAR LIQUIDS, 2020, 297

[22] Structural effect on the formation of hydrogen bonded complexes of benzyl amine and n-propyl amine with aromatic ethers through acoustic and thermodynamic parameters [J].

Hussain, S. G. Mohammed ;

Kumar, R. ;

Kannappan, V .

JOURNAL OF MOLECULAR STRUCTURE, 2022, 1247

[23] Structural effect on the strength of non-covalent interactions in binary mixtures of benzyl amine and certain ethers through ultrasonic, FT-IR spectral and DFT studies at 303.15 K [J].

Hussain, S. G. Mohammed ;

Kumar, R. ;

Ali, M. Mohamed Naseer ;

Kannappan, V. .

JOURNAL OF MOLECULAR LIQUIDS, 2019, 277 :865-875

[24]

Kaliszan R., 1987, Quantitative Structure-Chromatographic Retention Relationships

[25] Hydrogen bonding, base stacking, and steric effects in DNA replication [J].

Kool, ET .

ANNUAL REVIEW OF BIOPHYSICS AND BIOMOLECULAR STRUCTURE, 2001, 30 :1-22

[26]

LUDWIG A, 1990, CANCER RES, V50, P2470

[27] Evaluation of the cytotoxic, apoptosis inducing activity and molecular docking of spiroquinazolinone benzamide derivatives in MCF-7 breast cancer cells [J].

Mahdavi, Majid ;

Lavi, Malihe Mohseni ;

Yekta, Reza ;

Moosavi, Mohammad Amin ;

Nobarani, Mahnaz ;

Balalaei, Saeed ;

Arami, Sanam ;

Rashidi, Mohammad Reza .

CHEMICO-BIOLOGICAL INTERACTIONS, 2016, 260 :232-242

[28] Design, synthesis, and pharmacological evaluation of benzamide derivatives as glucokinase activators [J].

Mao, Weiwei ;

Ning, Mengmeng ;

Liu, Zhiqing ;

Zhu, Qingzhang ;

Leng, Ying ;

Zhang, Ao .

BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (09) :2982-2991

[29] Universal Solvation Model Based on Solute Electron Density and on a Continuum Model of the Solvent Defined by the Bulk Dielectric Constant and Atomic Surface Tensions [J].

Marenich, Aleksandr V. ;

Cramer, Christopher J. ;

Truhlar, Donald G. .

JOURNAL OF PHYSICAL CHEMISTRY B, 2009, 113 (18) :6378-6396

[30] Weak hydrogen bonding interaction S-H•••O=C studied by FT-IR spectroscopy and DFT calculations [J].

Mielcarek, Agnieszka ;

Dolega, Anna .

JOURNAL OF MOLECULAR STRUCTURE, 2016, 1103 :217-223

← 1 2 3 4 5 →