TY - JOUR
T1 - Electron density analyses of opioids
T2 - A comparative study
AU - Scheins, Stephan
AU - Messerschmidt, Marc
AU - Morgenroth, Wolfgang
AU - Paulmann, Carsten
AU - Luger, Peter
PY - 2007/6/28
Y1 - 2007/6/28
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=34547372867&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=34547372867&partnerID=8YFLogxK
U2 - 10.1021/jp0709252
DO - 10.1021/jp0709252
M3 - Article
C2 - 17530745
AN - SCOPUS:34547372867
SN - 1089-5639
VL - 111
SP - 5499
EP - 5508
JO - Journal of Physical Chemistry A
JF - Journal of Physical Chemistry A
IS - 25
ER -