Mass spectrometric investigation of the side-arm lariat effect of ortho- and para-methoxyphenoxymethyl-15-crown-5 in the gas phase

Mixtures of unsubstituted 15-crown-5 and its analogues containing ortho- and para-methoxyphenoxymethyl substituents with sodium salts were investigated by matrix assisted laser desorption/ionization (MALDI) mass spectrometry. Peaks of cationized molecules M+Na]⁺ and cluster ions 2M+2Na+An]⁺, where M is the crown ether molecule and An is monobasic acid anion, were observed in the mass spectra. It was shown that an increase of the shielding degree of the sodium cation in complexes with crown ethers, i.e., the lariat effect, led to a significant decrease in the intensity of peaks of the cluster ions.