Comparison of zwitterionic N-alkylaminomethanesulfonic acids to related compounds in the Good buffer series

• Robert D. Long,
• Newton P. Hilliard Jr,
• Suneel A. Chhatre,
• Tatiana V. Timofeeva,
• Andrey A. Yakovenko,
• Daniel K. Dei and
• Enoch A. Mensah

Beilstein J. Org. Chem. 2010, 6, No. 31, doi:10.3762/bjoc.6.31

• unstable at elevated temperature (as when autoclaving) – thus limiting their utility. Keywords: aminomethanesulfonate buffers; Good buffer; morpholinomethanesulfonic acid; pKa comparison; zwitterion; Introduction Some of the most widely used biological buffers are the compounds based on tertiary and

• aminomethanesulfonates, so our initial efforts were to synthesize the initial target compound N-morpholinomethanesulfonic acid (MMS) (1) by the reaction of morpholine with chloromethanesulfonic acid (Scheme 2). In spite of numerous attempts, this route produced no product, however. A subsequent literature search

• . alcohols (i.e. methanol, ethanol), as the materials are insoluble in other solvents. N-Morpholinomethanesulfonic acid [MMS (or MoMS)] (1). This was prepared as the half sodium salt by the general procedure from 0.200 mol of morpholine (17.4 mL), yielding 31.6 g (0.164 mol) of 1 (82% isolated yield) as a