Adduct formed by chromium trioxide and zwitterionic quinolinic acid

AbstractChromium trioxide forms an adduct with zwitterionic quinolinic acid. The structure of the product was found to be (quinolinium-3-carboxylato-O)trioxidochromium(VI), determined by single-crystal X-ray diffraction methods. To evaluate the bonding properties of the compound, its structure was optimized at the B3LYP/6-311G* level of theory. The electronic characteristics were investigated by topological methods applied to the total charge density in various model compounds including the title compound, title compound with a HF molecule presenting a hydrogen bonding and anionic moiety. Calculated aromaticity indices indicate that the quinolinic rings tend to conserve their degree of aromaticity against hydrogen bonding. However, when there is hydrogen bonding involving an N-H bond or when the quinolinium zwitterion is deprotonated, there are clear changes in the interaction between chromium trioxide and the quinolinic moiety.

[1]  J. Clyburne,et al.  Compounds of chromium(VI): The pyridine chromic anhydride complex, benzimidazolinium dichromate, and three 2-alkyl-1H-benzimida -zolinium dichromates , 2003 .

[2]  H. Krauss.  Chromylacetat — eine neue Chromyl‐Verbindung , 1958 .

[3]  M. Cyrański,et al.  Relation between the substituent effect and aromaticity. Part II. The case of meta‐ and para‐homodisubstituted benzene derivatives , 2006 .

[4]  R. Bader.  Atoms in molecules : a quantum theory , 1990 .

[5]  A. Katritzky,et al.  Aromaticity: a Theoretical Concept of Immense Practical Importance , 2000 .

[6]  A. Annila,et al.  Semipreparative synthesis, 13C- and 2D-NMR of Pulo'upone , 1993 .

[7]  M. Milčić,et al.  Are chelate rings aromatic? Calculations of magnetic properties of acetylacetonato and o-benzoquinonediimine chelate rings. , 2007, Inorganic chemistry.

[8]  Paul von Ragué Schleyer,et al.  Nucleus-Independent Chemical Shifts:  A Simple and Efficient Aromaticity Probe. , 1996, Journal of the American Chemical Society.

[9]  K. Gothelf,et al.  Asymmetric 1,3-Dipolar Cycloaddition Reactions. , 1998, Chemical reviews.

[10]  A. Katritzky,et al.  Quantitative measures of aromaticity for mono-, bi-, and tricyclic penta- and hexaatomic heteroaromatic ring systems and their interrelationships. , 2001, Chemical reviews.

[11]  T. Hase,et al.  Synthesis of Isopulo'upone , 1995 .

[12]  Louis J. Farrugia,et al.  ORTEP-3 for Windows - a version of ORTEP-III with a Graphical User Interface (GUI) , 1997 .

[13]  P. Schleyer,et al.  Dissected Nucleus-Independent Chemical Shift Analysis of π-Aromaticity and Antiaromaticity. , 2001, Organic letters.

[14]  F. S. Mathews,et al.  A semi-empirical method of absorption correction , 1968 .

[15]  C. López,et al.  3-Carboxypyridinium Dichromate (NDC) and (4-Carboxypyridinium Dichromate (INDC). Two New Mild, Stable, Efficient, and Inexpensive Chromium (VI) Oxidation Reagents , 1985 .

[16]  G. Sheldrick.  A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[17]  Tadeusz Marek Krygowski,et al.  Crystallographic studies of inter- and intramolecular interactions reflected in aromatic character of .pi.-electron systems , 1993, J. Chem. Inf. Comput. Sci..

[18]  J. Osborn,et al.  Chromyl complexes with aryloxy and siloxy ligands , 1990 .

[19]  Paul L. A. Popelier,et al.  Atoms in Molecules: An Introduction , 2000 .

[20]  Clémence Corminboeuf,et al.  Nucleus-independent chemical shifts (NICS) as an aromaticity criterion. , 2005, Chemical reviews.

[21]  Bernard Silvi,et al.  Computational Tools for the Electron Localization Function Topological Analysis , 1999, Comput. Chem..

[22]  Xavier Fradera,et al.  The Lewis Model and Beyond , 1999 .

[23]  Peter Pulay,et al.  Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations , 1990 .

[24]  G. Cardillo,et al.  Chromium Oxidations in Organic Chemistry , 1984 .

[25]  J. Dobado,et al.  Chemical Bonding in Hypervalent Molecules Revised. Application of the Atoms in Molecules Theory to Y3 X and Y3 XZ (Y = H or CH3; X = N, P or As; Z = O or S) Compounds , 1998 .

[26]  M. Solà,et al.  Relation between the substituent effect and aromaticity. , 2004, The Journal of organic chemistry.

[27]  Tadeusz Marek Krygowski,et al.  How H-Bonding Affects Aromaticity of the Ring in Variously Substituted Phenol Complexes with Bases. 4. Molecular Geometry as a Source of Chemical Information , 2004, J. Chem. Inf. Model..

[28]  Tadeusz M. Krygowski,et al.  Separation of the energetic and geometric contributions to the aromaticity. Part IV. A general model for the π-electron systems , 1996 .

[29]  W. Lewandowski,et al.  The application of Aj, BAC, I6, HOMA indexes for quantitative determination of aromaticity of metal complexes with benzoic, salicylic, nicotinic acids and benzene derivatives , 2006 .

[30]  T. Hase,et al.  The synthesis of haminols A and B , 1995 .

[31]  Friedrich Biegler-König,et al.  Calculation of the average properties of atoms in molecules. II , 1982 .

[32]  D. Mccain.  Inductive effects and Franck-Condon shifts in the visible spectra of substituted chromate ions , 1975 .

[33]  Glen B. Deacon,et al.  Relationships between the carbon-oxygen stretching frequencies of carboxylato complexes and the type of carboxylate coordination , 1980 .