Electron density analyses of opioids: A comparative study

Stephan Scheins, Marc Messerschmidt, Wolfgang Morgenroth, Carsten Paulmann, Peter Luger

Research output: Contribution to journalArticle

22 Scopus citations

Abstract

The electron densities of five morphine related molecules (codeine, diprenorphine, naltrexone in the neutral and protonated states, and dextromethorphan) were determined from high-resolution X-ray diffraction experiments (Mo Kα and synchrotron primary radiation) at low temperature and CCD area detection techniques. Bond topological analyses were applied, and a partitioning of the molecules into atomic regions making use of Bader's zero flux surfaces yielded atomic volumes and charges. The obtained atom and bonding properties were compared to the results of a previous experimental study of morphine and to theoretical calculations. Experimental and theoretical properties for all chemically equivalent bonds agree within an uncertainty range as is otherwise seen for different theoretical calculations. Hence, the transferability of chemically equivalent submolecular properties, being a key issue of the atoms in molecules (AIM) theory, has been verified experimentally in this class of chemically related molecules. On the other hand, topological differences could clearly be verified in regions with different chemical environments. Electron density differences between the two forms of naltrexone were examined and made visible in an extendend region around the nitrogen atom which is once in a neutral state and once in a positively charged state.

Original languageEnglish (US)
Pages (from-to)5499-5508
Number of pages10
JournalJournal of Physical Chemistry A
Volume111
Issue number25
DOIs
StatePublished - Jun 28 2007
Externally publishedYes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

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