Thermodynamics of Synthesis of New Phenoxazine Derivatives


 Phenoxazine, PM3 calculation, conformational structures, equilibrium constant, thermodynamics.

How to Cite

V. José Cotuá, Sandra Cotes, Fernando Castro, & Pedro Castro. (2013). Thermodynamics of Synthesis of New Phenoxazine Derivatives . Journal of Basic & Applied Sciences, 9, 16–20.


This article describes a semi-empirical study on the thermodynamics involved in the synthesis of three novel ortho, meta and para, potentially intercalatingphenoxazine 1 derivatives o-(6), m-(7) and p-(8). Quantum chemical calculations at the semi-empirical PM3 method were used in order to evaluate conformational states of the molecules, as well as to predict thermodynamic properties and equilibrium constants. The more favourable product was found to be the compound with the methoxy group in ortho-position. The methoxy group in para-position hinders the reaction by steric factor, which is reflected from the small constant, Kp.


Angyal SJ, Bullock E, Hanger WC, Havell J. Actinomycin. Part III. The reaction of actinomycin with alcali. J Chem Soc. 1957; 1592-602.

Mueller W, Crothers DM. Studies of the binding of actinomycin related compounds to DNA. J Mol Biol. 1968; 35:251-90

Vogler K, Lanz P. Synthesen in der polymyxin-reihe. 1. Miteilung. Synthese eines pentapeptid-fragmentes. Helv Chim Acta. 1960; 43: 270-9.

Ionescu M, Mantsch H, Katritzky AR, Boulton AJ. Advances in Heterocyclic Chemistry. 1967.Academic Press, New York, USA.

Sainsbury M. The Chemistry of Carbon Compounds. 2nd ed. Amsterdam; Coffey Elsevier 1978.

Gilmand H, Moore LO. The metalation of phenoxazine and some of its derivatives. J Am Chem Soc. 1958; 80: 2195-7.

Gilmand H, Shirley DA, Van Ess PR. Metalation of phenotiazine. J Am Chem Soc. 1944; 66: 625-7.

Weintein B, Crews O, Baker M, Goodman B. Potential anticancer agents LXX. Some simple derivatives of the actinomycins. J Org Chem. 1962; 27 (4): 1389-95.

Sheehan JG, Goodman M, Hess GP. Peptide derivatives containing hydroxyamino acids. J Am Chem Soc. 1956; 78: 1367-9.

Goldberg HI, Rabinowitz M. Actinomycin D inhibitich of desoxiribonucleic acid-dependent synthesis of ribonucleic acid. Science 1962; 136 (3513): 315-6.

Reich E, Shatkin F. Effect of actinomycin D on cellular nucleic acid synthesis and virus production. Science. 1961; 134: 556-7.

Jensen F. Introduction to Computational Chemistry. New York; John Wiley and Sons 1999.

Young D. Computational Chemistry. New York; John Wiley and Sons 2000.

Stewart JJP. Optimization of parameter for semiempirical methods. I. 1. Method. J Comp Chem. 1989; 10: 209-20

Halgren TA, Nachbar RB. Merch molecular force field. IV conformational energy and geometry for MMFF94. J Comput Chem. 1996;17: 587-615.<587::AID-JCC4>3.0.CO;2-Q

Jian FF, Zhang PS, Zheng Z. Ab initio and experimental studies on dibenzothiazyl disulfide. Bull Korean Chem Soc. 2006; 27: 1048-52.

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