Synthesis, spectral studies, molecular structure determination by single crystal X-ray diffraction of ( E )-1-(((3-fluor
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Synthesis, spectral studies, molecular structure determination by single crystal X‑ray diffraction of (E)‑1‑(((3‑fluoro‑4‑morpholinophenyl)imino)methyl)napthalen‑2‑ol and computational studies by Austin model‑1(AM1), MM2 and DFT/ B3LYP Dhananjay Rao Thandra1 · Rajeshwar Rao Bojja2 · Ramachandraiah Allikayala1 Received: 20 July 2020 / Accepted: 16 September 2020 © Springer Nature Switzerland AG 2020
Abstract (E)-1-(((3-fluoro-4-morpholinophenyl)imino)methyl)napthalen-2-ol (1) has been synthesized and its computational investigations have been carried out through semi-empirical Austin Model-1 (AM1), SCF-MM2 and DFT/B3LYP methods in relation to its solid state molecular structure determined by single-crystal X-ray diffraction to correlate structural parameters in the gaseous state under vacuum to empirical those of the molecule in its crystalline solid state. The compound is reported to crystallize in monoclinic system in space group P21/n with crystal data as a = 15.1589(12) Å, b = 7.4349(5) Å, c = 15.4287(13) Å, β = 98.340(4), V = 1720.5(2) Å3, Z = 4, density = 1.353 Mg/m3, F (000) = 736, T = 296(2) K, obtained through reflections collected/unique = 13,631/4112. The shifts in various relevant bond lengths, bond angles, dihedral angles, etc. under AM1, B3LYP and MM2 treatments are discussed. Graphic abstract (E)-1-(((3-fluoro-4-morpholinophenyl)imino)methyl)napthalen-2-ol has been synthesized and its structural aspects in its solid state obtained by single crystal XRD have been compared with those in its gas phase evaluated by Austin Model-1 under AM1, DFT/B3LYP and ChemSoft’s ChemDraw Pro under MM2 Calculations.
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s42452-020-03525-0) contains supplementary material, which is available to authorized users. * Ramachandraiah Allikayala, [email protected] | 1Department of Chemistry, National Institute of Technology Warangal, Warangal 506004, India. 2Kakatiya Thermal Power Project (O&M), Chelpur, Telangana State, India. SN Applied Sciences
(2020) 2:1765
| https://doi.org/10.1007/s42452-020-03525-0
Vol.:(0123456789)
Research Article
SN Applied Sciences
(2020) 2:1765
| https://doi.org/10.1007/s42452-020-03525-0
Keywords Schiff’s base · X-ray diffractometry · Semi-empirical calculations · DFT calculations · Conformational analysis
1 Introduction
2 Experimental
Schiff bases are known to have wide range of applications in the pharmacy, industry, electrochemistry, agriculture, etc.[1–10]. Morpholine and its phenyl substituted derivatives have been extensively utilized as antimalarial, antioxidant, antimicrobial, anti-inflammatory and analgesic properties [11–19]. The Schiff base complexes have been used in catalytic reactions [20, 21] and as models for biological system. Schiff bases generated with adduction of pharmaceutically useful chemical systems would be expected to offer synergic applications that can be evaluated by modern molecular modelling calculations. Austin Model-1 (AM1) is the semi-empirical method
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