Abstract
The structures, stabilities, and aromaticities of a series of (BCO) n (CH)4–n NH (n = 0–4), (BCO) n (CH)4–n O (n = 0–4), and (BCO) n (CH)4–n S (n = 0–4) clusters were investigated at the B3LYP density functional level of theory. The most stable positional isomers of the individual clusters were obtained. All of the calculated CO binding energies were exothermic, suggesting that these BCO-substituted species are stable. Calculated differences in strain energy between the BCO-substituted structures and their corresponding hydrocarbon clusters were all exothermic, indicating that the BCO-substituted structures are less strained. The negative nucleus-independent chemical shift (NICS) values obtained show that these BCO-substituted clusters are aromatic compounds, in good agreement with the aromaticities of the corresponding hydrocarbon species. To aid further experimental investigations, CO-stretching frequencies were also computed.
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References
Gmelin L (1976) Chapter 10. In: Gmelin handbuch der anorganischen chemie: borverbindungen (1–4, Suppl. 1980–1996, vol. 37). Springer, Berlin
Willner H, Aubke F (1997) Angew Chem Int Ed Engl 36:2402–2425
Burg BA, Schlesinger HI (1937) J Am Chem Soc 59:780–787
Finze M, Berndhardt E, Terheiden A, Berkei M, Willner H, Christen D, Oberhammer H, Aubke F (2002) J Am Chem Soc 124:15385–15398, and references therein
Zhou MF, Tsumor N, Andrews L, Xu Q (2002) J Am Chem Soc 124:12936–12937
Zhou M, Xu Q, Wang ZX, Schleyer PR (2002) J Am Chem Soc 124:14854–14855
Zhou M, Wang ZX, Schleyer PR (2003) ChemPhysChem 4:763–766
Hoffmann R (1982) Angew Chem Int Ed Engl 21:711–717
Papakondylis A, Miliordos E, Mavridis A (2004) J Phys Chem A 108:4335–4340
Maier G, Reisenauer HP, Henkelmann J, Kliche C (1988) Angew Chem Int Ed Engl 27:294–295
Cioslowski J, Hay PJ (1990) J Am Chem Soc 112:1707–1710
Wu HS, Jiao H, Wang ZX, Schleyer PR (2003) J Am Chem Soc 125:4428–4429
Wu HS, Qin XF, Xu XH, Jiao H, Schleyer PR (2005) J Am Chem Soc 127:2334–2338
Wang ZX, Chen ZF, Jiao H, Schleyer PR (2005) J Theo Comp Chem 4:669–688
Glossman MD (2001) J Mol Struct (THEOCHEM) 549:285–288
Feixas F, Matito E, Poater J, Solà M (2008) J Comput Chem 29:1543–1554
Schomaker V, Pauling L (1939) J Am Chem Soc 61:1769–1780
Bak B, Christensen D, Hansen L, Rastrup-Andersen J (1956) J Chem Phys 24:720–725
Nygaard L, Nielsen JT, Kirchheiner J, Maltesen G, Rastrup-Andersen J, Soerensen GO (1969) J Mol Struct 3(6):491–506
Mellouki A, Liévin J, Herman M (2001) Chem Phys 271:239–266
Cordell FR, Boggs JE (1981) J Mol Struct (THEOCHEM) 85:163–178
Schleyer PR, Maerker C, Dransfeld A, Jiao H, Hommes NJRE (1996) J Am Chem Soc 118:6317–6318
Schleyer PR, Jiao H, Hommes NJRE, Malkin VG, Malkina OL (1997) J Am Chem Soc 119:12669–12670
Schleyer PR, Manoharan M, Wang ZX, Kiran B, Jiao H, Puchta R, Hommes NJRE (2001) Org Lett 3:2465–2468
Wolinski K, Hinton JF, Pulay P (1990) J Am Chem Soc 112:8251–8260
Frisch MJ et al (2003) Gaussian 03. Gaussian, Inc., Pittsburgh
Rathke J, Schaefer R (1974) Inorg Chem 13:760–761
Strauss SH (1997) Chemtracts Inorg Chem 10(1997):77–103
Lupinetti AJ, Frenking G, Strauss SH (1998) Angew Chem Int Ed Engl 37:2113–2116
Acknowledgments
This work was supported by the National Natural Science Foundation of China (no. 2103103), the Natural Science Foundation of Shandong Province (no. ZR2011EL005), and the Natural Science Foundation of Ludong University (no. LY2010006). We acknowledge the support provided by Shan Xi Normal University for the calculations performed in this work.
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Qin, XF., Wang, F. & Wu, HS. Density functional studies of the stepwise substitution of pyrrole, furan, and thiophene with BCO. J Mol Model 19, 2309–2315 (2013). https://doi.org/10.1007/s00894-013-1766-3
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DOI: https://doi.org/10.1007/s00894-013-1766-3