Home Article Information
Iranian Journal of Chemistry and Chemical Engineering (IJCCE)
Journal Archive
Volume Volume 36 (2017)
Volume Volume 35 (2016)
Volume Volume 34 (2015)
Volume Volume 33 (2014)
Volume Volume 32 (2013)
Volume Volume 31 (2012)
Volume Volume 30 (2011)
Volume Volume 29 (2010)
Volume Volume 28 (2009)
Volume Volume 27 (2008)
Volume Volume 26 (2007)
Volume Volume 25 (2006)
Volume Volume 24 (2005)
Volume Volume 23 (2004)
Volume Volume 22 (2003)
Volume Volume 21 (2002)
Volume Volume 20 (2001)
Volume Volume 19 (2000)
Volume Volume 18 (1999)
Volume Volume 17 (1998)
Volume Volume 16 (1997)
Volume Volume 15 (1996)
Volume Volume 14 (1995)
Volume Volume 13 (1994)
Volume Volume 12 (1993)
Volume Volume 11 (1992)
Volume Volume 10 (1991)
Volume Volume 9 (1990)
Volume Volume 8 (1989)
Volume Volume 7 (1988)
Volume Volume 6 (1987)

Design of a New Nano Hinge Molecular Machine Based on Nitrogen Inversion: Computational Investigation

Article 2, Volume 35, Issue 1, Winter 2016, Page 11-15  XML PDF (431 K)
Document Type: Research Article
Authors
Sara Soleimani Gorgani1; Marjaneh Samadizadeh 2
1Young Researchers and Elite Club, Central Tehran Branch, Islamic Azad University, P.O. Box 13185-768 Tehran, I.R. IRAN
2Department of Chemistry, Faculty of Basic Sciences, Central Tehran Branch, Islamic Azad University, P.O. Box 13185-768 Tehran, I.R. IRAN
Abstract
 Ab initio calculations were employed to investigate nitrogen inversion as a configuration change that can supply an infinitely useful switchable control mechanism for some complex systems. In this paper, design of a new artificial molecular nanohinge is discussed based on nitrogen inversion in which reciprocating motion of substituent in effect of inversion phenomenon, led to an open–close motion in the molecule. Since the simple secondary amines easily face inversion process in the room temperature, a carboxamide derivative was selected as the initial driver for the molecular motion. The most critical finding from this study was that, following the displacement of the substituent attached to the amide nitrogen,making the xanthenes planar be dislocated and form hinge like reversible move.
Keywords
Nanohinge; Configuration changes; Nitrogen inversion; Amide; Ab initio calculations
Main Subjects
Computational Chemistry
References
[1] Credi A., Artificial Molecular Motors Powered by Light, Aust. J. Chem., 59: 157-169 (2006).

[2] Zheng Y. B., Hao Q., Yang Y-W., Kiraly B., Chiang I-K., Huang T. J., Light-driven Artificial Molecular Machines, J. Nanophoton., 4: 042501 (2010).

[3] Pathem B.K., Claridge S.A., Zheng Y.B., Weiss P.S., Molecular Switches and Motors on Surfaces, Annu. Rev.  Phys. Chem., 64: 605-630 (2013).

[4] Amrute-Nayak, M., Diensthuber, R.P., Steffen, W., Kathmann, D., Hartmann, F.K., Fedorov, R., Urbanke, C., Manstein, D.J., Brenner, B., Tsiavaliaris, G. Targeted Optimization of a Protein Nanomachine for Operation in Biohybrid Devices. Angew. Chem. Int. Ed, 122 (2): 322–326
(2010).

[5] Ghosh A., Fischer P. ,Controlled Propulsion of Artificial Magnetic Nanostructured Propellers, NanoLetters, 9(6): 2243-2245 (2009).

[6] Cavalcanti A., Shirinzadeh B., Zhang M., C. Kretly L., Nanorobot Hardware Architecture for Medical Defense, Sensors, 8: 2932-2958 (2008).

[7] Kinbara K., Aida T., Toward Intelligent Molecular Machines: Directed Motions of Biological and Artificial Molecules and Assemblies, Chem. Rev, 105 (4): 1377-1400 (2005).

[8] Kay E R., Leigh D A., Zerbetto F., Synthetic Molecular Motors and Mechanical Machines, Angew. Chem. Int. Ed, 46: 72-191 (2007).

[9] Knorr R., Ruhdorfer J., Mehlstäubl J., Böhrer P. Stephenson DS.,  (E, Z)1-Equilibria, 17 Demonstration of the Nitrogen Inversion Mechanism of Imines in a Schiff Base Mode, Eur. J. Inorg. Chem,  126: 747-754 (1993).

[10] Hough A. J., "Photochemical Control of Pyramidal Inversion and Photoactivation of Antimicrobial Agents", PhD Thesis, University of Warwick (2013).

[11] Park G., Kim S., Kang H., Substituents Effect on Aziridine Chemistry: N-Inversion Energy, Reactivity and Regioselectivity of Nucleophilic Ring-opening, Bull. Korean Chem. Soc, 26: 1339 (2005).

[12] Glaser R., Yin J., Miller S., Asymmetry in the N-Inversion of Heteroarene Imines: Pyrimidin-4(3H)-Imine, Pyridin-2(1H)-Imine, and 1H-Purine-6(9H)-Imine, J. Org. Chem., 75(4):1132-1142 (2010).

[13] Yavari I., Nouri-shargh D., Fallah Bagher Shaidaii H., Dadgar M., MNDO Study of Nitrogen Atom Inversion in Piperazine, N,N'-Dimethylpiperazine and N,N'-Dichloropiperazine, Iran. J. Chem. & Chem. Eng. (IJCCE), 16 (2): 63-67 (1997).

[14] Davies M.W., Shipman M., H.R. Tucker J., Walsh T.R.,Control of Pyramidal Inversion Rates by Redox Switching, J. Am. Chem. Soc. 128: 14260-14261 (2006).

[15] CAREY F A., SUNDBERG R J., “Advanced Organic Chemistry”, University of Virginia, Charlottesville, Virginia, (2007).

[16] Schmidt M.W., Baldridge K.K., Boatz J.A., Elbert S.T., Gordon M.S., Jensen J.H., Koseki S., Matsunaga N., Nguyen K.A., Su S., Windus T.L., Dupuis M., Montgomery J.A.,  General Atomic and Molecular Electronic Structure System, J. Comput. Chem.,14: 1347-1363 (1993)

Statistics
Article View: 856
PDF Download: 902