Abstract
The connections between the quantum chemical concept of local electron densities and the traditional concept of functional groups of organic chemistry are explored. The Density Domain criterion of functional groups and the Additive Fuzzy Density Fragmentation (AFDF) method are the tools for the construction of representative quantum chemical models for both local electron densities and functional groups. The applications of the method of fuzzy electron density partitioning of molecular electron density clouds to the description of the local fuzzy density contributions of functional groups are explored. The constraints implied by the recently proven “Holographic Electron Density Theorem” are discussed, with special emphasis on the predictability of differences in the activity of functional groups of a given type located within different molecular environments. The special role of symmetry and symmetry deficiency are discussed, and the deviations from local symmetry, as a diagnostic tool for the assessment of the reactivity of functional groups are explored.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Hohenberg P, Kohn W (1964) Phys Rev 136:B864
Levy M (1979) Proc Natl Acad Sci USA 76:6062
Levy M (1979) Bull Amer Phys Soc 24:626
Levy M (1982) Phys Rev A 26:1200
Levy M (1990) Adv Quant Chem 21:69
Hegerfeldt GC, Ruijsenaars SNM (1980) Phys Rev D 22:377
Foster JM, Boys SF (1960) Rev Mod Phys 32:300
Boys SF (1966) In: Löwdin P-O (ed) Quantum Theory of Atoms, Molecules and the Solid-state. Academic Press, New York
Edmiston C, Ruedenberg K (1963) Rev Mod Phys 35:457
Riess J, Münch W (1981) Theor Chim Acta 58:295
Pipek J, Mezey PG (1988) Internat J Quantum Chem Symp 22:1
Pipek J, Mezey PG (1989) J Chem Phys 90:4916
Schmidt MW (1997) GAMESS Quantum Chemistry Program Package Documentation (ISU Quantum Chemistry Group ISUQCG, Ames Laboratory-USDOE, Iowa State University, IA 50011 USA)
Mezey PG (1994) Canad J Chem 72:928 (Special issue dedicated to Prof J C Polanyi )
Mezey PG (1996) Functional Groups in Quantum Chemistry. In: Advances in Quantum Chemistry, Vol 27, p 163
Mezey PG (1996) Molecular Similarity Measures of Conformational Changes and Electron Density Deformations. In: Advances in Molecular Similarity, Vol 1, p 89
Mezey PG (1997) Fuzzy Measures of Molecular Shape and Size. In: Rouvray DH (ed) Fuzzy Logic in Chemistry, Academic Press, San Diego
Mezey PG (1997) Internat Rev Phys Chem 16:361
Mezey PG (1995) Density Domain Bonding Topology and Molecular Similarity Measures. In: Sen K (ed) Topics in Current Chemistry, Vol 173, Molecular Similarity. Springer-Verlag, Heidelberg, pp 63–83
Mezey PG (1995) J Math Chem 18:141
Mezey PG (1997) Int J Quantum Chem 63:39
Walker PD, Mezey PG (1993) J Amer Chem Soc 115:12423
Walker PD, Mezey PG (1994) J Amer Chem Soc 116:12022
Mezey PG (1999) Mol. Phys 96:169
Mezey PG (1998) J Math Chem 23:65
Mezey PG (to be published).
Luo X, Arteca GA, Zhang C, Mezey PG (1993) J Organometallic Chem 444:131
Walker PD, Mezey PG, Maggiora GM, Johnson MA, Petke JD (1995) J Comput Chem 16:1474
Walker PD, Maggiora GM, Johnson MA, Petke JD, Mezey PG (1995) J Chem Inf Comp Sei 35:568
Mezey PG, Zimpel Z, Warburton P, Walker PD, Irvine DG, Dixon DG, Greenberg B (1996) J Chem Inf Comp Sci 36:602
Du Q, Arteca GA, Mezey PG (1997) J Comp-Aided Mol Design 11:503
Mezey PG, Zimpel Z, Warburton P, Walker PD, Irvine DG, Huang X-D, Dixon DG, Greenberg BM (1998) Environ Toxicol Chem 17:1207
Mezey PG (1998) Molecular Structure-Reactivity-Toxicity Relationships. In: Huang PM (ed) Soil Chemistry and Ecosystem Health. SSSA Publ, Pittsburgh, PA, USA, pp 21–43
Du Q, Mezey PG (1998) J Comp-Aided Mol Design (in press)
Mezey PG (1999) J Chem Inf Comp Sci 39:224
Mezey PG (1999) Quantitative Shape-Activity Relations (QShAR), Molecular Shape Analysis, Charge Cloud Holography, and Computational Microscopy. In: Walker JD (ed) QSARs in Environmental Toxicology-VIII. QSARs for Predicting Endocrine Disruption, Chemical Persistence and Effects. SETAC Publ (in press)
Walker PD, Mezey PG (1994) Canad J Chem 72:2531
Walker PD, Mezey PG (1995) J Math Chem 17:203
Mezey PG, Walker PD (1997) Drug Discovery Today (Elsevier Trend Journal) 2:6
Mezey PG (1993) Shape in Chemistry: An Introduction to Molecular Shape and Topology. VCH Publishers, New York
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1999 Springer Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Mezey, P.G. (1999). Local Electron Densities and Functional Groups in Quantum Chemistry. In: Surján, P.R., et al. Correlation and Localization. Topics in Current Chemistry, vol 203. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-48972-X_9
Download citation
DOI: https://doi.org/10.1007/3-540-48972-X_9
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-65754-5
Online ISBN: 978-3-540-48972-6
eBook Packages: Springer Book Archive