Guanidines possesing different alkyl and/or aryl substituents represent a class of interesting neutral organic superbases applicable in wide variety of chemical reactions important in pharmaceutical industry, biodiesel production, synthesis of new biodegradable polymers etc. Therefore, design and synthesis of new derivatives with improved properties is highly desirable. Incorporation of the pyridine subunit into side chain provide additional functionality of the guanidines which are beneficial as a strong proton accepting unit capable of increasing proton affinities and as a unit that possess high affinity toward metal cations or anions. Whithin the proposed research project, gas-phase study of novel mono-, bis- and tris-alkylpyridine substituted guanidines and their interaction with metal cations and anions will be conducted by ESI-MS/MS technique and supported by modern ab initio and DFT calculations.