Abstract
A new parametrization for the Harmonic Oscillator Model of Aromaticity (HOMA) index to determine aromaticity of heterocycles is introduced. The new HOMA for Heterocycle Electron Delocalization (HOMHED) is based on the experimental data from electron diffraction X-ray for the reference molecules used to estimate the simple, double, and optimal bond lengths. Bond length of “pure” single and double bonds of non-conjugated systems or systems without π-electrons and/or n-electron delocalization were considered. The HOMHED index was determined for a series of five and six heterocycles with C–C, C–N, C–O, C–S, N–N, N–O, and N–S bonds. The π-electron delocalization of these heterocycles was determined by Krygowski-reformulated HOMA and HOMHED and it was proved that HOMHED worked in line with HOMA for all heterocycles, except those containing oxygen, which were found to be weak aromatic from Krygowski rHOMA calculations.
Graphical Abstract
The correlationship between Krygowski-reformulated HOMA (rHOMA) and a new parametrized model (HOMHED) for heterocyles is performed. It was proved that HOMHED worked in line with HOMA for all heterocycles, except those containing oxygen, which were found to be weak aromatic from rHOMA calculations.
Similar content being viewed by others
References
Kruszewski J, Krygowski TM (1972) Bull Acad Pol Sci Chim 20:907
Kruszewski J, Krygowski TM (1972) Tetrahedron Lett 13:3839
Krygowski TM, Kruszewski J (1973) Bull Acad Pol Sci Chim 21:409
Krygowski TM, Kruszewski J (1974) Bull Acad Pol Sci Chim 22:871
Krygowski TM (1993) J Chem Inf Comput Sci 33:70
Jug K, Koester A (1990) J Am Chem Soc 112:6772
Jeffrey GA (1987) Proc R Soc A 414:47
Krygowski TM, Cyrański MK (2001) Chem Rev 101:1385 and references cited therein
Cyrański MK (2005) Chem Rev 105:3773 and references cited therein
Raczyńska ED, Kosińska W, Ośmiałowski B, Gawinecki R (2005) Chem Rev 105: 3561 and references cited therein
Raczyńska ED (2005) Pol J Chem 79:749
Raczyńska ED, Ośmiałowski B, Gawinecki R (2005) Pol J Chem 79:1093
Raczyńska ED (2005) Pol J Chem 79:1003
Raczyńska ED, Krygowski TM, Zachara JE, Ośmiałowski B, Gawinecki R (2005) J Phys Org Chem 18:892
Osmialowski B, Raczyńska ED, Krygowski TM (2006) J Org Chem 71:3727
Raczyńska ED, Hallman M, Kolczyńska K, Stępniewski TM (2010) Symmetry 2:1485
Madura ID, Krygowski TM, Cyrański MK (1998) Tetrahedron 54:14913
Wodrich MD, Wannere CS, Mó Y, Jarowski PD, Houk KN, Schleyer PVR (2007) Chem Eur J 13:7731
Weinhold F (2001) Nature 411:539
Pophristic V, Goodman L (2001) Nature 411:565
Pophristic V, Goodman LJ (2002) Phys Chem A 106:1642
Mó Y, Wu W, Song LC, Lin MH, Zhang Q, Gao JL (2004) Angew Chem Int Ed 43:1986
Allen FH, Kennard O, Watson DG, Brammer L, Orpen G, Taylor R (1987) Perkin Trans 2:S1
Barten JA, Lork E, Röschenthaler G-V (2004) J Fluor Chem 125:1039
Mrozek A, Wojciechowska JK, Amiel P, Barbe J (2000) J Mol Struct 525:151
Mrozek A, Wojciechowska JK, Amiel P, Barbe J (2000) J Mol Struct 524:159
Mrozek A, Wojciechowska JK, Amiel P, Kieć-Kononowicz K (2003) J Mol Struct 397:403
Wojciechowska JK, Mrozek A, Czylkowski R, Tekiner-Gulbas B, Aki-Sener E, Yalçin I (2007) J Mol Struct 839:125
Chen Z, Wannere CS, Corminboueuf C, Puchta R, Schleyer PR (2005) Chem Rev 105:3842
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Frizzo, C.P., Martins, M.A.P. Aromaticity in heterocycles: new HOMA index parametrization. Struct Chem 23, 375–380 (2012). https://doi.org/10.1007/s11224-011-9883-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11224-011-9883-z