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

• 87701 10.3762/bjoc.6.31 Abstract Several N-alkyl and N,N-dialkylaminomethanesulfonic acids were synthesized (as zwitterions and/or sodium salts) to be tested for utility as biological buffers at lower pH levels than existing Good buffer compounds (aminoalkanesulfonates with a minimum of two carbons

• 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

• lower than their two and three carbon Good buffer counterparts (counting number of carbons between amine and sulfonic acid) and are well into the acidic pH range. All of the compounds except 2 show evidence of a systematic decrease in pKa as the number of carbons between the amine and sulfonic acid