Let's say we have $\ce{CH3-NH2}$ undergoing Hoffman's exhaustive methylation with $\ce{CH3-Cl}$. In which case side reactions such as $\ce{CH3-NH2 + CH3-NH2 -> CH3NHCH3 + NH3}$ would also occur.

How do we theoretically determine the relative difference in thermodynamic stability between the products of the side reaction ($\ce{CH3NHCH3 + NH3}$) and the main reaction?

  • $\begingroup$ I imagine it wouldn't dominate because we take methyl iodide in excess. $\endgroup$ – Sawarnik Aug 5 '17 at 19:51
  • $\begingroup$ Okay I'll make this question more specific $\endgroup$ – xasthor Aug 6 '17 at 2:31
  • $\begingroup$ The side reaction products will be more stable but would be kinetically unfeasible(comparitively high activation energy) $\endgroup$ – Ayushmaan Aug 7 '17 at 6:22
  • $\begingroup$ What is your side product: dimethyl amine (as suggested by the hydrogen on nitrogen)? The bonds of the leftmost carbon don’t add up … $\endgroup$ – Jan Aug 7 '17 at 9:50
  • $\begingroup$ @jan yes, made a mistake while typing this question sorry $\endgroup$ – xasthor Aug 7 '17 at 11:15

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