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Between methanethiol and methanol (if both species remain PROTONATED), I think methanethiol is the better base (ie, it is easier to form CH3CH2SH2+ than to form CH3CH2OH2+) because the lone pairs on the O are closer to the nucleus (O is more electronegative than S), so the O lone pairs are less available to reach out and grab a proton (aka they are less basic).


Between the DEPROTONATED forms, methoxide (CH3CH2O-) is definitely more basic than methanethiolate (CH3CH2S-). ?Methanol has a higher pKa than methanethiol by about 5 pH units).

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Q: What is a stonger base among methanthiolm and methanol?
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