Computational investigations, Hirshfeld surface analysis, interaction energy calculations, and energy framework crystal structure of methyl 2-amino-5-hydroxybenzoate

ЖСХ, т.62, №11, 2021, стр.1857

Received: April, 20, 2021
Revised: June, 17, 2021
Accepted for publication: June, 21, 2021
DOI 10.26902/JSC_id83815
Views: 249

¹ Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan

² Department of Physics, Faculty of Science, Hacettepe University, Beytepe-Ankara, Turkey

³ Department Chemie, Fakultät fur Naturwissenschaften, Universität Paderborn, Paderborn, Germany

⁴ CEQUINOR, Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, La Plata , Buenos Aires, República Argentina

The title compound with the molecular formula C₈H₉NO₃ is synthesized by refluxing 2-amino-5-hydroxybenzoic acid in methanol. The molecular structure of the compound is determined by single crystal X-ray diffraction. Methyl 2-amino-5-hydroxybenzoate crystallizes in the orthorhombic space group P2₁2₁2₁ with a = 4.973(2) Å, b = 10.923(5) Å, c = 14.074(6) Å, Z = 4 and V = 764.4(6) Å³. DFT is used to compute HOMO—LUMO energy levels, to predict the reactivity of substituents (NH₂ and OH), and to determine the nucleophilic character of these two groups. The orientation and nature of substituents on benzene favors the formation of a stable six-membered ring via hydrogen bonding which plays a key role in the properties of the investigated compound. The natural bond orbital (NBO) population analysis demonstrates that the hyperconjugative effect between the donor lone pairs located on the carbonyl oxygen atom and the N—H group, via the lp O → σ*(N—H) 1,6-remote interaction, is responsible for the preferred conformation. The molecular electrostatic potential (MEP) surface shows the electrical neutrality in the molecule. To get an insight to the intermolecular interactions in the crystal a Hirshfeld surface analysis is also carried out.

Keywords: methyl-2-amino-5-hydroxybenzoate, crystal structure, DFT, Hirshfeld surface analysis, MEP analysis

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Computational investigations, Hirshfeld surface analysis, interaction energy calculations, and energy framework crystal structure of methyl 2-amino-5-hydroxybenzoate

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