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Structure, antibacterial activity and theoretical study of 2-hydroxy-1-naphthaldehyde-N-methylethanesulfonylhydrazone

✍ Scribed by Neslihan Özbek; Gülten Kavak; Yusuf Özcan; Semra İde; Nurcan Karacan

Publisher
Elsevier Science
Year
2009
Tongue
English
Weight
456 KB
Volume
919
Category
Article
ISSN
0022-2860

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✦ Synopsis

2-Hydroxy-1-naphthaldehyde-N-methylethanesulfonylhydrazone was synthesized and its structure was investigated by X-ray diffraction, IR, NMR and mass spectroscopies. It crystallizes in the monoclinic system, space group P2 1 /c, a = 22.712(4), b = 5.793(4), c = 11.032(2) Å, a = 90.0, b = 102.070(8)°, c = 90.0°, V = 1419.4(1) Å 3 , Z = 4. Spectroscopic assignment and calculations carried out using B3LYP/6-31G ** basis set and crystallographic results indicate the predominance of the phenol-imine tautomeric form. It has strong intramolecular hydrogen bond of type OAH N [with distance donor-acceptor 2.579(4) Å]. The angular disposition of the bonds about the sulfur atom significantly deviates from that of a regular tetrahedron as expected. This deviation can be attributed to the non-bonded interactions involving the S@O bonds and methyl groups in both molecular and crystal structure. Result of conformational analysis was also compared with crystallographic data. Antimicrobial activity of the title compound was screened against E. coli

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