Guest–Host Interaction of Coinage Metals in π-Rich Cavities
Zhi Xiang Wong A and Matthias Lein A B
+ Author Affiliations
- Author Affiliations
A School of Chemical and Physical Sciences, Victoria University of Wellington, Wellington 6012, New Zealand.
B Corresponding author. Email: matthias.lein@vuw.ac.nz
Australian Journal of Chemistry 69(9) 969-974 https://doi.org/10.1071/CH16208
Submitted: 31 March 2016 Accepted: 7 May 2016 Published: 1 June 2016
Abstract
The complexation of coinage metal cations with [2.2.2]paracyclophane and deltaphane has been investigated by means of density functional theory (DFT) calculations employing the PBE0-D3 hybrid functional, which incorporates explicit dispersion corrections to account for the weak intermolecular forces that are important in the systems studied. Natural bond orbital (NBO) analyses, Bader's Atoms in Molecules theory analyses as well as localised molecular orbital – energy decomposition analyses (LMO-EDAs) have been carried out to further investigate the electronic structure and bonding of the complexes. It was found that both cyclophanes bind strongest with gold ions, followed closely by copper ions and lastly silver ions. The two fragments interact in a non-covalent fashion in these complexes and the metal preferentially resides at the periphery of the molecular cavity of the cyclophane.
References
[1] J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, Comprehensive Supramolecular Chemistry Vol. 1 1996 (Pergamon: Oxford).[2] F. Vögtle, C. Seel, P.-M. Windscheif, Comprehensive Supramolecular Chemistry Vol. 2 1996 (Pergamon: Oxford).
[3] F. N. Diederich, Cyclophanes 1991 (Royal Society of Chemistry: Cambridge).
[4] C. J. Brown, A. C. Farthing, Nature 1949, 164, 915.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG3cXht1Cqsg%3D%3D&md5=e192d964a9f915a31adae4b7ecc54713CAS |
[5] I. Tabushi, H. Yamada, Z. Yoshida, R. Oda, Tetrahedron 1971, 27, 4845.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3MXlsFWmurc%3D&md5=f588478b7639c5d1c8f724e22ddd11f8CAS |
[6] Y. Miyahara, T. Inazu, T. Yoshino, Tetrahedron Lett. 1983, 24, 5277.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2cXht1SltL8%3D&md5=2799e7870499480bb83be7cd2237cbb7CAS |
[7] S.-T. Lin, F.-M. Yang, D. W. Liang, J. Chem. Soc., Perkin Trans. 1 1999, 1725.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXjsFOqs7c%3D&md5=47deb0c43465d4e0665ee583cc23fcd9CAS |
[8] S.-T. Lin, F.-M. Yang, W.-F. Tien, J. Chem. Res. (S) 1999, 1999, 608.
| Crossref | GoogleScholarGoogle Scholar |
[9] S.-T. Lin, F.-M. Yang, L.-H. Lin, Tetrahedron 1997, 53, 16123.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXnsFantro%3D&md5=f232f3ef703f6bcc6082917f5b314717CAS |
[10] F.-M. Yang, S.-T. Lin, J. Org. Chem. 1997, 62, 2727.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXisFeqsbs%3D&md5=43c4ada4a643808c1ed4060cad96d1a1CAS | 11671631PubMed |
[11] N. K. Dalley, X. Kou, R. A. Bartsch, P. Kus, J. Incl. Phenom. Macro. 2003, 45, 139.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXkvFCqt7w%3D&md5=715f94dd9b38a99e198a17023bac7fbdCAS |
[12] C. Cohen-Addad, M. Lebars, A. Renault, Acta Crystallogr. 1984, 40, 1927.
[13] T. Seppälä, E. Wegelius, K. Rissanen, New J. Chem. 1998, 22, 789.
| Crossref | GoogleScholarGoogle Scholar |
[14] T. Lahtinen, E. Wegelius, K. Rissanen, New J. Chem. 2001, 25, 905.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXksF2msLc%3D&md5=785fd46e8f5e61dd245cc8744084edd8CAS |
[15] J.-L. Pierre, P. Baret, P. Chautemps, M. Armand, J. Am. Chem. Soc. 1981, 103, 2986.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3MXksVajsr8%3D&md5=14c0d0171cddab80d496a28d4d288c3aCAS |
[16] H. Kang, A. Hanson, B. Eaton, V. Boekelheide, J. Am. Chem. Soc. 1985, 107, 1979.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2MXhsVyrt7o%3D&md5=aece90d6c0839198a2586adf2be9ea6fCAS |
[17] C. Cohen-Addad, P. Baret, P. Chautemps, J.-L. Pierre, Acta Crystallogr. Sect. C: Struct. Chem. 1983, 39, 1346.
| Crossref | GoogleScholarGoogle Scholar |
[18] M. Munakata, L. P. Wu, T. Kuroda-Sowa, M. Maekawa, Y. Suenaga, S. Nakagawa, J. Chem. Soc., Dalton Trans. 1996, 1525.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XisFOrsrY%3D&md5=ae34163746ce66dfa9c349155713933bCAS |
[19] J. C. Garrison, R. S. Simons, W. G. Kofron, C. A. Tessier, W. J. Youngs, Chem. Commun. 2001, 1780.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXmvFCitLs%3D&md5=bd68ba27bf3b8cee99f37907938b7d9eCAS |
[20] Y.-C. Yang, S.-T. Lin, W.-S. Chen, J. Chem. Res. (S) 2008, 2008, 280.
| Crossref | GoogleScholarGoogle Scholar |
[21] G. L. Guillet, F. T. Sloane, D. M. Ermert, M. W. Calkins, M. K. Peprah, E. S. Knowles, E. Cizmar, K. A. Abboud, M. W. Meisel, L. J. Murray, Chem. Commun. 2013, 49, 6635.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtVWmtb%2FN&md5=2c405ebefb6eae41c486bf85e43c2574CAS |
[22] M. V. Baker, D. H. Brown, R. A. Haque, B. W. Skelton, A. H. White, Dalton Trans. 2010, 39, 70.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhsFChsrjJ&md5=70f0d031a2aaa79bb6efe446f1436f93CAS |
[23] M. B. Inoue, F. Medrano, M. Inoue, A. Raitsimring, Q. Fernando, Inorg. Chem. 1997, 36, 2335.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXivFSitb8%3D&md5=9ef31ae561d660394e4498b72ff82d7eCAS | 11669869PubMed |
[24] J.-T. Hou, Q.-F. Zhang, B.-Y. Xu, Q.-S. Lu, Q. Liu, J. Zhang, X.-Q. Yu, Tetrahedron Lett. 2011, 52, 4927.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtVKjtbrN&md5=05004d2b18400389e6dc762150cdf594CAS |
[25] K. Raatikainen, J. Huuskonen, K. Rissanen, Dalton Trans. 2011, 40, 5706.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXmsVagtbc%3D&md5=ddc845adddb2f69b40f2be1a030e17f3CAS | 21505693PubMed |
[26] J. Gross, G. Harder, A. Siepen, J. Harren, F. Vögtle, H. Stephan, K. Gloe, B. Ahlers, K. Cammann, K. Rissanen, Chem. – Eur. J. 1996, 2, 1585.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXlsFequw%3D%3D&md5=26fd86eba7435fe5f71a39dd00194ef1CAS |
[27] J. Bobacka, T. Lahtinen, J. Nordman, S. Häggström, K. Rissanen, A. Lewenstam, A. Ivaska, Electroanalysis 2001, 13, 723.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXkslegu7k%3D&md5=bac2b25b3d3d9a267e2a088c13e9efcbCAS |
[28] Y. Okada, F. Ishii, Y. Kasai, J. Nishimura, Tetrahedron Lett. 1993, 34, 1971.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXkt1Ors7g%3D&md5=1f8c6a7bd83df4f512343590c899d5f7CAS |
[29] T. Yamato, M. Haraguchi, J.-i. Nishikawa, S. Ide, J. Chem. Soc., Perkin Trans. 1 1998, 609.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXht1Srtrg%3D&md5=73bea4755485078cf24e72fabb6ce213CAS |
[30] Y. Okada, M. Mizutani, F. Ishii, J. Nishimura, Tetrahedron Lett. 1999, 40, 1353.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXhtFymtbs%3D&md5=75c6d425fed053b03e15bb0f3d2a0c08CAS |
[31] S. Inokuma, M. Kuramami, S. Otsuki, T. Shirakawa, S.-i. Kondo, Y. Nakamura, J. Nishimura, Tetrahedron 2006, 62, 10005.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XptlCkt7o%3D&md5=ad6a316933ed943bfd9cb0c59291ec06CAS |
[32] B. Valeur, I. Leray, Coord. Chem. Rev. 2000, 205, 3.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXmtVantb4%3D&md5=6de38146e4b53f4f4e3b6f5e7aeba691CAS |
[33] M. B. Inoue, P. Oram, G. Andreu-de Riquer, M. Inoue, P. Borbat, A. Raitsimring, Q. Fernando, Inorg. Chem. 1995, 34, 3528.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXmtVyitbs%3D&md5=8c352c60d0244fb7c668de2540f0588eCAS |
[34] M. B. Inoue, H. Santacruz, M. Inoue, Q. Fernando, Inorg. Chem. 1999, 38, 1596.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXhsVars7g%3D&md5=a5445dcaa953f56a289fbb8d7bcac210CAS |
[35] M. B. Inoue, I.C.M. Noz, L. Machi, M. Inoue, Q. Fernando, Inorg. Chim. Acta 2000, 311, 50.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXhvVKhs7c%3D&md5=f44e53ff51bda6a0d9024ab52ab12b7fCAS |
[36] M. B. Inoue, M. Inoue, R. Sugich-Miranda, L. Machi, E. F. Velazquez, Q. Fernando, Inorg. Chim. Acta 2001, 317, 181.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXjslaltbw%3D&md5=9d9590fc8f787f26779e7000032ce512CAS |
[37] M. V. Baker, M. J. Bosnich, C. C. Williams, B. W. Skelton, A. H. White, Aust. J. Chem. 1999, 52, 823.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXhsleisg%3D%3D&md5=9e7584d329e1f79d4105ec30d9ca2495CAS |
[38] M. V. Baker, B. W. Skelton, A. H. White, C. C. Williams, J. Chem. Soc., Dalton Trans. 2001, 111.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXpvVWitA%3D%3D&md5=f0cbfd92f783781f003dde6f286ad0baCAS |
[39] E. Alcalde, C. Ayala, I. Dinarès, N. Mesquida, F. Sánchez-Ferrando, J. Org. Chem. 2001, 66, 2281.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXhs1agtrk%3D&md5=80ec8ce46fc6b63deab4b466d7c7aefdCAS | 11281767PubMed |
[40] J. C. Garrison, R. S. Simons, J. M. Talley, C. Wesdemiotis, C. A. Tessier, W. J. Youngs, Organometallics 2001, 20, 1276.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXhsV2msL4%3D&md5=5d43da0d36c178e6b655ce5ece68d405CAS |
[41] E. Alcalde, N. Mesquida, L. Pérez-García, S. Ramos, M. Alemany, M. L. Rodríguez, Chem. – Eur. J. 2002, 8, 474.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XhtVyisrw%3D&md5=6896caadce63fa6bd7b1d0f2993c6dc8CAS | 11843160PubMed |
[42] R. S. Simons, J. C. Garrison, W. G. Kofron, C. A. Tessier, W. J. Youngs, Tetrahedron Lett. 2002, 43, 3423.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XjtVertbY%3D&md5=34faaffd21b4c502fe7cb3fea17e5ba8CAS |
[43] Y. Yuan, G. Gao, Z.-L. Jiang, J.-S. You, Z.-Y. Zhou, D.-Q. Yuan, R.-G. Xie, Tetrahedron 2002, 58, 8993.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XotlWgtbw%3D&md5=6bdb208df3eb50cd408465a1d9c34c80CAS |
[44] M. V. Baker, S. K. Brayshaw, B. W. Skelton, A. H. White, C. C. Williams, J. Organomet. Chem. 2005, 690, 2312.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXjsFyksL8%3D&md5=e98cbed1dadd4f1068f8acbe9a957597CAS |
[45] M. V. Baker, D. H. Brown, R. A. Haque, P. V. Simpson, B. W. Skelton, A. H. White, C. C. Williams, Organometallics 2009, 28, 3793.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXmsFWmurw%3D&md5=dbb2f5abbbc2ba463245de33bf9b37faCAS |
[46] C. E. Willans, K. M. Anderson, P. C. Junk, L. J. Barbour, J. W. Steed, Chem. Commun. 2007, 3634.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXps1Grsb0%3D&md5=9d6b52d285cc70275c2e2b7165d8abe3CAS |
[47] V. Amendola, M. Boiocchi, B. Colasson, L. Fabbrizzi, M.-J. Rodriguez Douton, F. Ugozzoli, Angew. Chem. Int. Ed. 2006, 45, 6920.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtFOks7nF&md5=27ef726bc3452b2b0d7fe895c2d6ac6cCAS |
[48] V. Amendola, M. Boiocchi, L. Fabbrizzi, N. Fusco, Eur. J. Org. Chem. 2011, 2011, 6434.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtFOlsLzN&md5=da66cafebfb8b746a967c486b76b21a2CAS |
[49] P. Saarenketo, R. Suontamo, T. Jödicke, K. Rissanen, Organometallics 2000, 19, 2346.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXjtFyht7o%3D&md5=b4d27e17921c259a6f2c6e5a09a4a7e1CAS |
[50] P. Saarenketo, R. Suontamo, K. Rissanen, Organometallics 2002, 21, 5473.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XotlOmuro%3D&md5=3cd9db8b3f46754ad3e6b37bd8375c5eCAS |
[51] H. R. Dias, M. Fianchini, T. R. Cundari, C. F. Campana, Angew. Chem. Int. Ed. 2008, 47, 556.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXptVCguw%3D%3D&md5=5a383bc50bf64750efa61314a94682dbCAS |
[52] M. Fianchini, C. F. Campana, B. Chilukuri, T. R. Cundari, V. Petricek, H. V. R. Dias, Organometallics 2013, 32, 3034.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXns1aiur8%3D&md5=514fb81814987a34493cc34cd7c71aeeCAS |
[53] I. Krossing, A. Reisinger, Angew. Chem. Int. Ed. 2003, 42, 5725.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXpvFaitbc%3D&md5=4ca49649f827eabbe68a44f64898ba3cCAS |
[54] J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1996, 77, 3865.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XmsVCgsbs%3D&md5=80e9e7f93c4d868c24426c2d2790225cCAS | 10062328PubMed |
[55] J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1997, 78, 1396.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXht1Gns7o%3D&md5=d3bf3af88893c60749d96d5d1f065d41CAS |
[56] C. Adamo, V. Barone, J. Chem. Phys. 1999, 110, 6158.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXitVCmt7Y%3D&md5=eb685a60ae227e8a03f08433e846a77eCAS |
[57] S. Grimme, J. Antony, S. Ehrlich, H. Krieg, J. Chem. Phys. 2010, 132, 154104.
| Crossref | GoogleScholarGoogle Scholar | 20423165PubMed |
[58] S. Grimme, S. Ehrlich, L. Goerigk, J. Comput. Chem. 2011, 32, 1456.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXjsF2isL0%3D&md5=738d507a3e0a68831e1f4257fbe0c764CAS | 21370243PubMed |
[59] F. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys. 2005, 7, 3297.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXpsFWgu7o%3D&md5=53637d0dcdd0b147563ee4cae4e3b387CAS | 16240044PubMed |
[60] D. Andrae, U. Haeussermann, M. Dolg, H. Stoll, H. Preuss, Theor. Chim. Acta 1990, 77, 123.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXkt12ntLo%3D&md5=fbfc81d44eae379c7ce3f1c65d070596CAS |
[61] M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09 Revision B.1 2009 (Gaussian Inc.: Wallingford, CT.)
[62] T.A. Keith, AIMAll (Version 13.05.06). 2013 (TK Gristmill Software: Overland Park, KS).
[63] R. F. W. Bader, Atoms in Molecules: A Quantum Theory 1990 (Clarendon Press: Oxford).
[64] J. P. Foster, F. Weinhold, J. Am. Chem. Soc. 1980, 102, 7211.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3cXmtFSmsbw%3D&md5=04628299bdd41c9591cbd3dd826ded2eCAS |
[65] A. E. Reed, F. Weinhold, J. Chem. Phys. 1983, 78, 4066.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3sXhs1Ohtbc%3D&md5=3e005d4be79ec04d40fd74b69d22d199CAS |
[66] A. E. Reed, R. B. Weinstock, F. Weinhold, J. Chem. Phys. 1985, 83, 735.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2MXltFSisLY%3D&md5=9a88dfbc50c12ddb816b619b6e8fa884CAS |
[67] A. E. Reed, F. Weinhold, J. Chem. Phys. 1985, 83, 1736.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2MXlsVOhu7w%3D&md5=51fb02bf5d8c8ed5b0e9fb07b6684785CAS |
[68] J. E. Carpenter, F. Weinhold, J. Mol. Struct. THEOCHEM 1988, 169, 41.
[69] A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1cXmtlOitbw%3D&md5=395c47d723905e2ee2b85abbf63ea776CAS |
[70] F. Weinhold, J. E. Carpenter, in The Structure of Small Molecules and Ions (Eds R. Naaman, Z. Vager) 1988, pp. 227–236 (Plenum Press: New York, NY).
[71] (a) E. D. Glendening, J. K. Badenhoop, A. E. Reed, J. E. Carpenter, J. A. Bohmann, C. M. Morales, C. R. Landis, F. Weinhold, NBO 6.0 2013 (Theoretical Chemistry Institute, University of Wisconsin: Madison, WI).
(b) E. D. Glendening, C. R. Landis, F. Weinhold, , J. Comput. Chem. 2013, 34, 1429.
| Crossref | GoogleScholarGoogle Scholar |
[72] G. Camiletti, A. Canal-Neto, F. E. Jorge, S. F. Machado, J. Mol. Struct. THEOCHEM 2009, 122, 910.
[73] P. J. P. de Oliveira, C. L. Barros, F. E. Jorge, A. Canal-Neto, M. Campos, J. Mol. Struct. THEOCHEM 2010, 43, 948.
[74] A. Canal-Neto, F. E. Jorge, Chem. Phys. Lett. 2013, 158, 582.
[75] P. Su, H. Li, J. Chem. Phys. 2009, 131, 014102.
| Crossref | GoogleScholarGoogle Scholar | 19586091PubMed |
[76] M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. J. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. Su, T. L. Windus, M. Dupuis, J. A. Montgomery, J. Comput. Chem. 1993, 14, 1347.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXhsFaqtQ%3D%3D&md5=e3532055f2c3f4e19509fba5111418d0CAS |
[77] C.Y. Legault, CYLview. 1.0b 2009, Université de Sherbrooke. Available at: http://www.cylview.org.
