Editing Methadone (section)

=== Conformation ===
The protonated form of methadone takes on an extended conformation, while the free base is more compact. In particular, it was found that there is an interaction between the tertiary amine and the carbonyl carbon of the ketone function (R<sub>3</sub>N ••• >C=O) that limits the molecule's conformation freedom, though the distance (291 pm by X-ray) is far too long to represent a true chemical bond. However, it does represent the initial trajectory of attack of an amine on a carbonyl group and was an important piece of experimental evidence for the proposal of the [[Bürgi–Dunitz angle]] for carbonyl addition reactions.<ref>{{cite journal | vauthors = Bürgi HB, Dunitz JD, Shefter E | title = Pharmacological implications of the conformation of the methadone base | journal = Nature | volume = 244 | issue = 136 | pages = 186–187 | date = August 1973 | pmid = 4516455 | doi = 10.1038/newbio244186b0 }}</ref>