Results of the theoretical conformational analysis of 14-crown-4 are presented. Conformational analysis was performed using molecular mechanics (MM3) and using two conformational search techniques. The lowest energy minima obtained are submitted to HF/6-31G** calculations, and further optimized. Results are discussed with emphasis on the importance of intramolecular interactions, and the energetic order of conformations is explained on the basis of findings for 1,2-dimethoxyethane and 1,3-dimethoxypropane.