The interaction energies between glycoluril clip and thiophenol derivatives using density functional theory calculations

References

• Smeets JWH, Sijbesma RP, Niele FGM, Spek AL, Smeets WJJ, Nolte RJM. Novel concave building block for the synthesis of organic hosts. J Am Chem Soc. 1987;109:928–929. doi: 10.1021/ja00237a064
   Web of Science ®Google Scholar
• Azam A, Chawla HM, Pandey S. A novel dansyl-appended glycoluril-based fluorescence sensor for silver ions. Tetrahedron Lett. 2010;51:4710–4711. doi: 10.1016/j.tetlet.2010.07.005
   Web of Science ®Google Scholar
• Sheng-Li H, Neng-Fang S, Guo-Dong Y, Hui-Zhen G, An-Xin W, Chu-Luo Y. Synthesis, structural characterization, and fluorescent chemosensory properties of novel molecular clips based on diethoxycarbonyl glycoluril. Tetrahedron Lett. 2007;48:1591–1594. doi: 10.1016/j.tetlet.2006.12.138
   Web of Science ®Google Scholar
• Kang J, Jo J-h, In S. Carboxylate anion selective receptor with glycoluril molecular scaffold. Tetrahedron Lett. 2004;45:5225–5228. doi: 10.1016/j.tetlet.2004.05.040
   Web of Science ®Google Scholar
• Hof F, Craig SL, Nuckolls C, Rebek J. Molecular encapsulation. J Angew Chem Int Ed. 2002;41:1488–1508. doi: 10.1002/1521-3773(20020503)41:9<1488::AID-ANIE1488>3.0.CO;2-G
   PubMed Web of Science ®Google Scholar
• Day A, Arnold AP, Blanch RJ, Snushall BJ. Controlling Factors in the synthesis of cucurbituril and its homologues. J Org Chem. 2001;66:8094–8100. doi: 10.1021/jo015897c
   PubMed Web of Science ®Google Scholar
• Pinn-Tsong C, Nai-Chia C, Chien-Chen L, Sheng-Hsien C. Direct observation of mixed-valence and radical cation dimer states of tetrathiafulvalene in solution at room temperature: association and dissociation of molecular clip dimers under oxidative control. Chem Eur J. 2008;14:6546–6552. doi: 10.1002/chem.200800213
   PubMed Web of Science ®Google Scholar
• Lin J, Zhang Y, Zhang J, Xue S, Zhu Q, Tao Z. Synthesis of partially methyl substituted cucurbit[n]urils with 3a-methyl-glycoluril. J Mol Struc. 2008;875:442–446. doi: 10.1016/j.molstruc.2007.05.017
   Web of Science ®Google Scholar
• Sijbesma RP, Kentgens APM, Nolte RJM. Binding of dihydroxybenzenes in a synthetic molecular clip: effect of hydrogen bonding and .pi.-stacking. J Org Chem. 1991;56:3199–3201. doi: 10.1021/jo00010a001
   Web of Science ®Google Scholar
• Sijbesma RP, Kentgens APM, Lutz ETG, Van der Maas JH, Nolte RJM. Binding features of molecular clips derived from diphenylglycoluril. J Am Chem Soc. 1993;115:8999–9005. doi: 10.1021/ja00073a015
   Web of Science ®Google Scholar
• Reek JNH, Priem AH, Engelkamp H, Rowan AE, Elemans JAAW, Nolte RJM. Binding features of molecular clips. Separation of the effects of hydrogen bonding and π−π interactions. J Am Chem Soc. 1997;119:9956–9964. doi: 10.1021/ja970805f
   Web of Science ®Google Scholar
• Gieling GTW, Scheeren HW, Israel R, Nolte RJM. Synthesis and physical properties of novel guanidine containing molecular clips. Strong host–guest binding and formation of a lyotropic liquid crystalline phase. Chem Commun. 1996;2:241–243. doi: 10.1039/cc9960000241
   Web of Science ®Google Scholar
• Rowan AE, Elemans JAAW, Nolte RJM. Molecular and supramolecular objects from glycoluril. Acc Chem Res. 1999;32:995–1006. doi: 10.1021/ar9702684
   Web of Science ®Google Scholar
• Rezaei-Seresht E, Hokmabadi F. First immobilization of a glycoluril-derived molecular clip on merrifield resin: facile separation of dihydroxybenzenes by affinity chromatography. Tetrahedron Lett. 2010;51:2473–2476. doi: 10.1016/j.tetlet.2010.02.154
   Web of Science ®Google Scholar
• Becke AD. Density-functional thermochemistry. III. The Role of Exact Exchange. J Chem Phys. 1993;98:5648–5652. doi: 10.1063/1.464913
   Web of Science ®Google Scholar
• Lee C, Yang W, Parr RG. Development of the Colle–Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B. 1988;37:785–789. doi: 10.1103/PhysRevB.37.785
   PubMed Web of Science ®Google Scholar
• Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JAJr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian 03 (Revision B 03). Pittsburgh: Gaussian. Inc; 2003.
   Google Scholar
• Becke AD. Density-functional exchange-energy approximation with correct asymptotic behavior. Phys Rev A. 1988;38:3098–3100. 1988;38:3098–3100. doi: 10.1103/PhysRevA.38.3098
   PubMed Web of Science ®Google Scholar
• Vessally E, Hokmabadi F. A study of the interaction energy between a glycoluril molecular clip and dihydroxybenzenes or diaminobenzenes: a justification for easy separation by affinity chromatography. Tetrahedron Lett. 2012;53:5645–5648. doi: 10.1016/j.tetlet.2012.08.033
   Web of Science ®Google Scholar