A C18 Quaternary Ammonium Library

A library of precursor and functionally active quaternary ammonium cations (QACs) for use as corrosion resistant and or antimicrobial coatings, or alternatively as polymer modifiers, is described. High yielding and improved routes to a series of functionally terminated allyl ([(CH2= CH-CH2) (m)-N+(Me) (n)-C18H37] [X (-)], 1: m= 1, n= 2, X- = Br (-), 3: m= 2, n= 1, X (-) = 1 (-), 4: m= 3, n= 0, X (-) = Br-) vinyl ([CH2= CHCH2CH2-N+ Me-2-C18H37][Br (-)] 5), hydroxy ([HO-(CH2) m-N+ Me-2-C18H37][Br (-)], 6: m= 3, 7: m= 4), haloalkyl ([X1-(CH2) (3)-N+ Me-2-C18H37][X (-)] 8: X-1 = Br, X= Br-, 9: X-1 = Cl, X= I (-)), dimethoxyphenethyl ([(MeO) 2C6H3(CH2) (2)-N+ Me-2-C-18 H-37][Br-], 11), acetamido ([H3C(O) NH-(CH2) (3)-N+ Me-2-C18H37][Cl (-)],12) cyano ([N = C-CH2-N+ Me-2-C18H37][Cl (-)], 13), organocarbony-lamino ([R-C(O) 2NH-(CH2) (3)-N+ Me-2-C18H37][Br (-)], 14: R= t-Bu-, 15: R= PhCH2-), phthalimido ([PhthN-(CH2) (3)-N+ Me-2-C18H37][Br (-)], 16), amino ([H2N-(CH2) (3)-N+ Me-2-C18H37][Br (-)] 17), acetylthio ([HC(O) S(CH2) (3)-N+ Me-2-C18H37][Cl (-)], 18), thiol ([HS-(CH2) 3-N+ Me-2-C18H37] [Cl (-)] 19), disulfa ([-S-(CH2) (2)-N+ Me-2-C18H37] (2)[Br-] 2, 20) C-18 QACs prepared by thermal and or microwave driven Menshutkin reactions are detailed. All new compounds were characterized by NMR spectroscopy, HRMS spectrometry and in the case of 1 and 6 by X-ray crystallography.