Computational study of noncovalent interactions within the various complexes of para aminosalicylic acid and Cr 2+ , Mn
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Computational study of noncovalent interactions within the various complexes of para aminosalicylic acid and Cr2+, Mn+, Fe2+, Co+, Ni2+, Cu+, Zn2+ cations: exploration of the enhancing effect of the cation–π interaction on the intramolecular hydrogen bond Fahimeh Alirezapour1 · Azadeh Khanmohammadi1 Received: 11 July 2020 / Accepted: 11 November 2020 © Springer-Verlag GmbH Germany, part of Springer Nature 2020
Abstract The quantum chemical calculations are performed to investigate the effect of cation–π interactions on structural and electronic characterization of the various complexes of para aminosalicylic acid with mono- ( Mn+, Co+, Cu+) and divalent ( Cr2+, Fe2+, Ni2+, Zn2+) metal cations. Topological analysis of the atoms in molecules is applied to evaluate the nature of the considered interactions. Electron populations obtained from the natural bond orbital analysis also give insight into the electron nature of the studied systems. The achieved outcomes from calculations show that the strongest/weakest interactions belong to the divalent/monovalent complexes. Besides, one O–H···O intramolecular hydrogen bond (H-bond) is observed in the analyzed complexes. Our findings indicate that the H-bond of complexes is placed in the medium H-bonds category. In addition, it can be stated that the O–H···O H-bond is strengthened/weakened by cation–π interactions in the presence of divalent/monovalent complexes. The energy gap, electronic chemical potential, chemical hardness, softness, and electrophilicity index are also calculated by using frontier molecular orbitals. Keywords Para aminosalicylic acid · Cation–π · Hydrogen bond · AIM · NBO
1 Introduction The 4-aminosalicylic acid, also known as para aminosalicylic acid (PAS), is an anti-tuberculosis antibiotic [1]. PAS is an analog of para-aminobenzoic acid that is salicylic acid substituted by an amino group at position 4. This medication is used in combination with other drugs. It is often administered in association with isoniazid. In fact, PAS is the second antibiotic found to be effective in the treatment of tuberculosis, after streptomycin. It works by stopping or slowing the growth of bacteria. This antibiotic treats only bacterial infections. It is not used for viral infections (such as common
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00214-020-02700-1) contains supplementary material, which is available to authorized users. * Fahimeh Alirezapour [email protected] 1
Department of Chemistry, Payame Noor University, P.O. Box 19395‑3697, Tehran, Iran
cold, flu). Furthermore, PAS is believed to apply by blocking the ability of bacteria to make folic acid [2]. It is also used in the treatment of inflammatory bowel disease (ulcerative colitis and Crohn’s disease) [3]. PAS is contraindicated for patients with serious renal disease due to buildup of toxic metabolites, especially the acetylated forms [4]. Noncovalent interactions such as H-bonding, π–π, cation–π, h
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