The dipole moments and the structures of chloro- and bromo-crotonolactones

The dipole moments of the isomeric pairs of bromocrotonolactones and of chlorocrotonolactones were measured in benzene solutions at 25° along with those of butyrolactone and crotonolactone. Based on the observed moments of the last two compounds, theoretical calculations were made of the moments of these halocrotonolactones for both - and β-modifications. The comparison between the observed and calculated moments showed definitely that, of the isomeric pair of bromocrotonolactones, one having a greater moment 4·70 D and a lower melting point 57° is the -modification and the other isomer having a moment of 3·86 D and a melting point of 77° is the β-modification. Similarly, -chlorocrotonolactone shows a moment of 4·83 D and melts at 27° while the corresponding β-modification has a moment of 3·57 D and a melting point of 51–52·5°. The result is in good agreement with the conclusion derived from the infra-red absorptions of these compounds and affords an unequivocal evidence in favour of the correctness of the reasoning advanced by Gilman et al., by Whiting, and by Owen and Sultanbawa agains the presumption of Hill and his followers. Thus, the long pending problem on the constitutional formulae of isomeric - and β-halocrotonolactones has been settled.