tag:blogger.com,1999:blog-9633767.post8390476709217093021..comments2024-03-25T09:11:17.877-07:00Comments on The Curious Wavefunction: Why are secondary amines the most basic?Wavefunctionhttp://www.blogger.com/profile/14993805391653267639noreply@blogger.comBlogger5125tag:blogger.com,1999:blog-9633767.post-56593344207827783042015-01-14T20:57:55.695-08:002015-01-14T20:57:55.695-08:00Thanks for your valuable solution. This has been o...Thanks for your valuable solution. This has been one of my curious doubts in chemistry. Anonymoushttps://www.blogger.com/profile/01347160459329773752noreply@blogger.comtag:blogger.com,1999:blog-9633767.post-7787313832064344222015-01-14T20:57:07.938-08:002015-01-14T20:57:07.938-08:00Thanks for your valuable solution. This has been o...Thanks for your valuable solution. This has been one of my curious doubts in chemistry. Anonymoushttps://www.blogger.com/profile/01347160459329773752noreply@blogger.comtag:blogger.com,1999:blog-9633767.post-40239956447773675542010-11-05T14:19:36.758-07:002010-11-05T14:19:36.758-07:00I believe that the (aqueous) solubility enhancemen...I believe that the (aqueous) solubility enhancement of observed for N-methylation of secondary amides is a crystal packing effect rather than due to changes in basicity. The observation that N-methylation of cyclic secondary amides does not lead to significant enhancement of solubility supports this view.Peter Kennyhttps://www.blogger.com/profile/12180360326821860667noreply@blogger.comtag:blogger.com,1999:blog-9633767.post-51182096825750202912010-11-04T18:27:15.634-07:002010-11-04T18:27:15.634-07:00True. That's a factor too. I guess it's im...True. That's a factor too. I guess it's implicitly included in 'solvation'.Wavefunctionhttps://www.blogger.com/profile/14993805391653267639noreply@blogger.comtag:blogger.com,1999:blog-9633767.post-13937624726469253702010-11-04T18:24:57.724-07:002010-11-04T18:24:57.724-07:00It's long been known that secondary amides are...It's long been known that secondary amides are typically more soluble than primary amides (so long as the alkyl groups are small).<br /><br />I was told that the reason for this is that secondary amides can only serve as H-bond acceptors, while primary amides can be both donors and acceptors. Thus, the intermolecular forces between secondary amides are weaker, which makes them easier to disrupt during solubilization.Paulhttp://blog.chembark.comnoreply@blogger.com