1. bookVolume 10 (2017): Issue 2 (October 2017)
Journal Details
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10 Dec 2012
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2 times per year
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English
access type Open Access

Theoretical study of a series of phenol derivatives: molecular properties vs. cytotoxicity

Published Online: 29 Dec 2017
Page range: 91 - 95
Journal Details
License
Format
Journal
First Published
10 Dec 2012
Publication timeframe
2 times per year
Languages
English

The quantum chemical calculations using DFT were performed for 2-alkyl-4X and 2,6-dialkyl-4-X substituted phenols. Based on the optimal geometries the bond dissociation enthalpies (BDEs), proton enthalpies (PAs) and the lipophilicities were computed. Additionally, simple geometry parameter was found correlating well with experimental leukemia cell toxicity of substituted phenols. Next, we have found no linear dependence between PA or BDE values and log1/C values in gas phase or in water despite the radical toxicity mechanism proposed in the literature.

Keywords

Atkins PW (1998) Physical Chemistry, 6th ed. Oxford University Press, Oxford.Search in Google Scholar

Becke AD (1988) Phys Rev A 38: 3098-3100.Search in Google Scholar

Bizarro MM, Cabral BJC, dos Santos RMB, Simões JAM (1999) Pure Appl Chem 71: 1249-1256.Search in Google Scholar

Borges dos Santos RM, Martinho Simões JA (1998) J Phys Chem Ref Data 27: 707-739. Cheminformatics, Molinspiration. Bratislava, Slovak Republic. 2016.Search in Google Scholar

Clark T, Chandrasekhar J, Spitznagel GW, Schleyer PVR (1983) J Comp Chem 4: 294-301.Search in Google Scholar

Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr., Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Keith T, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J and Fox DJ (2009) Gaussian 09, Revision D.01, Gaussian, Inc. Wallingford CT.Search in Google Scholar

Ghamali M, Chtita S, Adad A, Hmamouchi R, Bouachrine M, Lakhlifi T (2015) J Mater Environ Sci 6: 280-288.Search in Google Scholar

Krishnan RBJS, Binkley JS, Seeger R, Pople JA (1980) J Chem Phys 72: 650-654.Search in Google Scholar

Lee C, Yang W, Parr RG (1988) Phys Rev B 37: 785-789.Search in Google Scholar

Marenich AV, Cramer CJ, Truhlar DG (2009) J Phys Chem B 113: 6378.Search in Google Scholar

McLean AD, Chandler GS (1980) J Chem Phys 72: 5639-5648.Search in Google Scholar

Ong CN, Lee BL, Shi CY, Ong HY, Lee HP (1994) Int J Cancer 59: 177-180.Search in Google Scholar

Parker VD (1992) J Am Chem Soc 114: 7458-7462.Search in Google Scholar

Selassie CD, De Soyza TV, Rosario M, Gao H, Hansch C (1998) Chem-bio Interact 113: 175-190.Search in Google Scholar

Selassie C, Shusterman A, Verma R (1999) J Chem Soc Perk Trans 2: 2729-2733.Search in Google Scholar

Selassie CD, Verma RP, Kapur S, Shusterman AJ, Hansch C (2002) J Chem Soc Perk Trans 2: 1112-1117.Search in Google Scholar

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