Abstract
Extraction experiments in the two-phase water/nitrobenzene system and γ-activity measurements were used to determine the stability constant of a hexaarylbenzene-based receptor/pyridinium complex dissolved in nitrobenzene saturated with water. Further, applying quantum mechanical calculations, the most probable structure of this “asymmetrical” cationic complex was derived.
Graphical Abstract
Similar content being viewed by others
References
Watson MD, Fechtenkötter A, Müllen K (2001) Chem Rev 101:1267
Rathore R, Burns CL (2003) J Org Chem 68:4071
Petty MC, Bryce MR, Bloor D (1995) Introduction to molecular electronics. Oxford University Press, New York
Maiya BG, Ramasarma T (2001) Curr Sci 80:1523
Shukla R, Lindeman SV, Rathore R (2006) J Am Chem Soc 128:5328
Shukla R, Lindeman SV, Rathore R (2007) Org Lett 9:1291
Ma JC, Dougherty DA (1997) Chem Rev 97:1303
Armentrout PB, Rodgers MT (2000) J Phys Chem A 104:2238
Gapeev A, Yang CN, Klippenstein SJ, Dunbar RC (2000) J Phys Chem A 104:3246
Tsuzuki S, Yoshida M, Uchimaru Y, Mikami M (2001) J Phys Chem A 105:769
Huang H, Rodgers MT (2002) J Phys Chem A 106:4277
Mo Y, Subramanian G, Gao J, Ferguson DM (2002) J Am Chem Soc 124:4832
Reddy AS, Sastry GN (2005) J Phys Chem A 109:8893
Vijay D, Sastry GN (2008) Phys Chem Chem Phys 10:582
Sakurai K, Mizuno T, Hiroaki H, Gohda K, Oku J, Tanaka T (2005) Angew Chem Int Ed 44:6180
Makrlík E, Dybal J, Vaňura P (2009) Monatsh Chem 140:251
Makrlík E, Dybal J, Vaňura P (2009) Monatsh Chem 140:1289
Makrlík E, Dybal J, Vaňura P (2010) Monatsh Chem 141:1191
Dybal J, Makrlík E, Vaňura P (2010) Monatsh Chem 141:15
Dybal J, Makrlík E, Vaňura P (2009) J Radioanal Nucl Chem 279:253
Makrlík E, Toman P, Vaňura P (2011) J Radioanal Nucl Chem 289:667
Makrlík E, Toman P, Vaňura P (2012) J Radioanal Nucl Chem 292:1137
Makrlík E, Toman P, Vaňura P (2013) J Radioanal Nucl Chem 295:615
Makrlík E, Dybal J, Vaňura P (2013) J Radioanal Nucl Chem 295:1299
Makrlík E, Toman P, Vaňura P (2013) Monatsh Chem 143:199
Makrlík E, Toman P, Vaňura P (2013) J Radioanal Nucl Chem 295:1119
Makrlík E, Toman P, Vaňura P (2013) J Radioanal Nucl Chem 295:1887
Hawthorne MF, Young DC, Andrews TD, Howe DV, Pilling RL, Pitts AD, Reintjes M, Warren LF, Wegner PA (1968) J Am Chem Soc 90:879
Makrlík E, Vaňura P (1985) Talanta 32:423
Rais J (1971) Collect Czech Chem Commun 36:3253
Makrlík E, Božek F (1998) Polish J Chem 72:949
Makrlík E, Selucký P, Vaňura P, Budka J (2010) J Radioanal Nucl Chem 286:155
Makrlík E, Hálová J, Kyrš M (1984) Collect Czech Chem Commun 49:39
Makrlík E, Vaňura P (1998) ACH Models Chem 135:213
Makrlík E, Vaňura P, Daňková M (1999) J Radioanal Nucl Chem 240:579
Makrlík E, Vaňura P (2006) Monatsh Chem 137:157
Makrlík E, Toman P, Vaňura P, Selucký P, Rathore R (2010) J Radioanal Nucl Chem 286:55
Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785
Becke AD (1993) J Chem Phys 98:5648
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 Jr JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, 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 Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, Revision C.01. Gaussian Inc, Wallingford
Kříž J, Dybal J, Makrlík E, Budka J, Vaňura P (2009) J Phys Chem A 113:5896
Kříž J, Toman P, Makrlík E, Budka J, Shukla R, Rathore R (2010) J Phys Chem A 114:5327
Kříž J, Dybal J, Makrlík E, Vaňura P, Moyer BA (2011) J Phys Chem B 115:7578
Toman P, Makrlík E, Vaňura P (2012) Monatsh Chem 143:985
Makrlík E, Toman P, Vaňura P (2013) Monatsh Chem 144:919
Acknowledgments
This work was supported by the Grant Agency of Faculty of Environmental Sciences, Czech University of Life Sciences, Prague, Project No.: 42900/1312/3114 “Environmental Aspects of Sustainable Development of Society”, and by the Czech Ministry of Education, Youth, and Sports (Project MSM 6046137307). The authors of this study thank Dr. Petr Toman from Prague for some theoretical calculations. Finally, R.R. thanks the National Science Foundation for financial support.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Makrlík, E., Vaňura, P. & Rathore, R. Experimental and theoretical study on the interaction of the pyridinium cation with a hexaarylbenzene-based receptor. Monatsh Chem 146, 521–525 (2015). https://doi.org/10.1007/s00706-014-1370-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-014-1370-y