Aromaticity of benzenoid hydrocarbons with inserted –B=B– and –BH–BH– groups: a comparison

详细信息    查看全文

• 作者：Krzysztof K. Zborowski ; Ibon Alkorta ; Jose Elguero
• 关键词：Aromaticity ; Substituted benzenoid hydrocarbons ; Boron compounds ; HOMA ; NICS
• 刊名：Structural Chemistry
• 出版年：2016
• 出版时间：February 2016
• 年：2016
• 卷：27
• 期：1
• 页码：91-99
• 全文大小：559 KB
• 参考文献：1.Omelchenko IV, Shishkin OV, Gorb L, Leszczynski J, Fias S, Bultinck P (2011) Chem Phys Phys Chem 13:20536–20548CrossRef
  2.Dou C, Saito S, Matsuo K, Hisaki I, Yamaguchi S (2012) Angew Chem Int Ed 51:12206–12210CrossRef
  3.Roszak R, Roszak S (2015) J Mol Model 21:28CrossRef
  4.Sánchez-Sanz G (2015) Tetrahedron 71:826–839CrossRef
  5.Karabiyik H, Sevinçek R, Karabiyik H (2015) J Phys Org Chem 28:490–496CrossRef
  6.Tejchman W, Proniewicz LM, Zborowski KK (2015) J Phys Org Chem 28:536–541CrossRef
  7.Moezzi A, Bartlett RA, Power PP (1992) Angew Chem Int Ed 31:1082–1083CrossRef
  8.Moezzi A, Olmstead MM, Power PP (1992) J Am Chem Soc 114:2717–2719CrossRef
  9.Grigsby WJ, Power PP (1996) Chem Commun 1996:2235–2236CrossRef
  10.Grigsby WJ, Power PP (1997) Chem Eur J 3:368–375CrossRef
  11.Nöth H, Knizek J, Ponikwar W (1999) Eur J Inorg Chem 1999:1931–1937CrossRef
  12.Bissinger P, Braunschweig H, Damme A, Kupfer T, Vargas A (2012) Angew Chem Int Ed 51:9931–9934CrossRef
  13.Poater J, Solà M, Vinas C, Teixidor F (2013) Chem Eur J 19:4169–4175CrossRef
  14.Poater J, Solà M, Vinas C, Teixidor F (2014) Angew Chem Int Ed 53:12191–12195CrossRef
  15.Pauling L, Pauling P (1975) Chemistry. W. H. Freeman and Company, San Francisco
  16.Wiberg E, Holleman AF (2001) Inorganic chemistry. Elsevier, Amsterdam
  17.Vogel W (1994) Glass chemistry. Springer-Verlag GmbH, BerlinCrossRef
  18.Cotton FA, Wilkinson G, Gaus PL (1987) Basic inorganic chemistry. Wiley, New York
  19.Zborowski KK, Alkorta I, Elguero J, Proniewicz LM (2012) Struct Chem 23:595–600CrossRef
  20.Zborowski KK, Alkorta I, Elguero J, Proniewicz LM (2013) Struct Chem 24:543–548CrossRef
  21.Ponikvar-Svet M, Zeiger DN, Keating LR, Liebman JF (2013) Struct Chem 24:2101–2114CrossRef
  22.Boese R, Maulitz AH, Stellberg P (1994) Chem Ber 127:1887–1889CrossRef
  23.Aihara J, Kanno H, Ishida T (2005) J Am Chem Soc 127:13324–13330CrossRef
  24.Yu HL, Sang RL, Wu YY (2009) J Phys Chem A 113:3382–3386CrossRef
  25.Del Bene JE, Yanez M, Alkorta I, Elguero J (2009) J Chem Theory Comput 5:2239–2247CrossRef
  26.Kiran BK, Kumar GG, Nguyen MT, Kandalam AK, Jena P (2009) Inorg Chem 48:9965–9967CrossRef
  27.Ruman T, Jarmuła A, Rode W (2010) Bioorg Chem 38:242–245CrossRef
  28.Qiang C, Hui B, Jin-Chang G, Chang-Qing M, Si-Dian L (2011) Phys Chem Chem Phys 13:20620–20626CrossRef
  29.PvR Schleyer, Jiao H (1996) Pure Appl Chem 68:209–218
  30.Krygowski TM, Cyrański MK, Czarnocki Z, Häfelinger G, Katritzky AR (2000) Tetrahedron 56:1783–1796CrossRef
  31.Poater J, Durán M, Solà M, Silvi B (2005) Chem Rev 105:3911–3947CrossRef
  32.Cyrański MK, Krygowski TM, Katritzky AR, Schleyer PvR (2002) J Org Chem 67:1333–1338CrossRef
  33.Feixas F, Matito E, Poater J, Solà M (2007) J Phys Chem A 111:4513–4521CrossRef
  34.Kruszewski J, Krygowski TM (1972) Tetrahedron Lett 13:3839–3842CrossRef
  35.PvR Schleyer, Marker C, Dransfeld A, Jiao HJ, Hommes NJRV (1996) J Am Chem Soc 118:6317–6318CrossRef
  36.Corminboeuf C, Heine T, Seifert G (2004) Schleyer PvR. Phys Chem Chem Phys 6:273–276CrossRef
  37.Poater J, Fradera X, Duran M, Solà M (2003) Chem Eur J 9:400–406CrossRef
  38.Dauben HJ Jr, Wilson JD, Laity JL (1968) J Am Chem Soc 90:811–813CrossRef
  39.Krygowski TM (1993) J Chem Inf Comput Sci 33:70–78CrossRef
  40.Bader RFW (1990) Atoms in molecules: a quantum theory. Oxford University Press, Oxford
  41.AIMAll, Version 11.10.16, Keith TA (2011) TK Gristmill Software, Overland Park (aim.tkgristmill.com)
  42.Becke AD (1993) J Chem Phys 98:5648–5653CrossRef
  43.Krishnan R, Binkley JS, Seeger R, Pople JA (1980) J Chem Phys 72:650–655CrossRef
  44.Gaussian 09, Revision A.02, 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, 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 O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian, Inc., Wallingford
  45.Bodwell GJ, Bridson JN, Cyrański MK, Kennedy JWJ, Krygowski TM, Mannion MR, Miller DO (2003) J Org Chem 68:2089–2098CrossRef
  46.Zborowski KK, Krygowski TM (2014) Tetrahedron Lett 55:6539–6561CrossRef
  
• 作者单位：Krzysztof K. Zborowski (1)
  Ibon Alkorta (2)
  Jose Elguero (2)
  
  1. Faculty of Chemistry, Jagiellonian University, 3 Ingardena Street, 30-060, Kraków, Poland
  2. Instituto de Química Médica (C.S.I.C.), Juan de la Cierva 3, 28006, Madrid, Spain
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Computer Applications in Chemistry
  Physical Chemistry
  Theoretical and Computational Chemistry
  
• 出版者：Springer Netherlands
• ISSN：1572-9001

文摘

Structures of selected polycyclic conjugated hydrocarbons with –B=B– and –BH–BH– moieties inserted in different places were calculated at the B3LYP/6-311++G** level and their aromatic properties evaluated. HOMA, NICS(0), NICS(1)zz, Λ and PDI indices were used for studying their aromatic properties. Both optimized planar (as in parent hydrocarbons) and non-planar structures were taken into account. It is shown that insertion of both types of boron groups disturbs and decreases the aromaticity of the corresponding hydrocarbons. The decreasing effect of the –BH–BH– group is much stronger. What is quite intriguing is that it appears that non-planar structures of the studied compounds have a little higher aromaticity than the strictly planar ones. Mutual correlations between results obtained by different aromaticity indices are calculated and thoroughly discussed. Keywords Aromaticity Substituted benzenoid hydrocarbons Boron compounds HOMA NICS