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Molecules 2014, 19(6), 8414-8433; doi:10.3390/molecules19068414

Synthesis, Crystal Structure, DFT Studies and Evaluation of the Antioxidant Activity of 3,4-Dimethoxybenzenamine Schiff Bases

1
Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA, 42300 Puncak Alam Campus, Malaysia
2
School of Fundamental Science, Universiti Malaysia Terengganu, 21030 Kuala Terengganu, Malaysia
3
Faculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia
4
Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, 75270 Karachi, Pakistan
5
Institute of Advance Research Studies in Chemical Sciences, University of Sindh Jamshoro, Hyderabad 76080, Pakistan
6
Department of Chemistry, Faculty of Science, Universiti Malaya, 50603 Kuala Lumpur, Malaysia
*
Author to whom correspondence should be addressed.
Received: 8 May 2014 / Revised: 4 June 2014 / Accepted: 12 June 2014 / Published: 19 June 2014
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Abstract

Schiff bases of 3,4-dimethoxybenzenamine 125 were synthesized and evaluated for their antioxidant activity. All the synthesized compounds were characterized by various spectroscopic techniques. In addition, the characterizations of compounds 13, 15 and 16 were supported by crystal X-ray determinations and their geometrical parameters were compared with theoretical DFT calculations at the B3LYP level of theory. Furthermore, the X-ray crystal data of two non-crystalline compounds 8 and 18 were theoretically calculated and compared with the practical values of compounds 13, 15, 16 and found a good agreement. The compounds showed good DPPH scavenging activity ranging from 10.12 to 84.34 μM where compounds 14 and 6 showed stronger activity than the standard n-propyl gallate. For the superoxide anion radical assay, compounds 13 showed better activity than the standard. View Full-Text
Keywords: 3,4-dimethoxybenzenamine Schiff bases; crystal structure; DFT calculation; antioxidant activity 3,4-dimethoxybenzenamine Schiff bases; crystal structure; DFT calculation; antioxidant activity
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Aziz, A.N.; Taha, M.; Ismail, N.H.; Anouar, E.H.; Yousuf, S.; Jamil, W.; Awang, K.; Ahmat, N.; Khan, K.M.; Kashif, S.M. Synthesis, Crystal Structure, DFT Studies and Evaluation of the Antioxidant Activity of 3,4-Dimethoxybenzenamine Schiff Bases. Molecules 2014, 19, 8414-8433.

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