sp2雜化問題一問，（鹼性強度）的問題，請高手入

No, sp3 amine is more basic than sp2 imine.As the percent s character increases the electrons are held more
closely to the positively charged nucleus, therefore an sp2 hybridized amine hold the electrons closer than sp3 hybridized amine
thus the sp2 hybridized amine relatively does not want to donate the electron density
sp3 amines are therefore more basic than sp2 amines
http://www.utdallas.edu/~biewerm/19.pdf


2011-04-06 17:32:52 補充：
Show me the download link of this problem.
The basicity of sp3 amine is stronger than sp2 amine and no doubt about it.
http://en.wikibooks.org/wiki/Structural_Biochemistry/Organic_Chemistry/Organic_Functional_Group/Amino

2011-04-06 17:32:57 補充：
http://www.chtf.stuba.sk/~szolcsanyi/education/files/Organicka%20chemia%20II/Predn%E1%9Aka%201_Am%EDny_Vlastnosti%20a%20pr%EDprava/Doplnkov%E9%20%9Atudijn%E9%20materi%E1ly/Structure%20and%20Properties%20of%20Amines_Sibi.pdf

2011-04-06 17:33:09 補充：
Hybridization Effects on Amine Basicity
Nitrogen lone pairs in sp orbitals are closest to the nucleus and are thus the most stable
and least basic. Nitrogen lone pairs in sp3 orbitals are furthest from the nucleus, least
stable, and most basic.

2011-04-06 17:33:22 補充：
http://homepage.mac.com/tminehan/spring334pdfs/20&21&22Anew.pdf

2011-04-06 17:35:35 補充：
http://www.docstoc.com/docs/25357549/pyridine-pyrrole-and-basicity

Yy,
in sp3-hybridized amine, lone pair in sp3-orbital is used to accept the H(+).
then in sp2-hybridized imine, the lone pair in which orbital will accept the H(+)? the hybridized one, or the unhybridized one?

the unhybridized one should have energy higher than the hybridized one.. ?

2011-04-13 11:15:30 補充：
basicity: triethylamine > pyridine >> pyrrole

i think your problem is related to aromaticity of the molecule. say, basicity of aromatic amines.
basicity of pyridine is weaker than those of aliphatic amine, reason as stated by Yy.

2011-04-13 11:19:08 補充：
yet, protonation of pyridine does not disrupt the aromaticity of it, so the ion is not destabilized as much.

pyrrole, however, accepts the H(+) by the lone-pair in unhybridized p-orbital. protonation would destroy the aromaticity of it, strongly destabilizing the ion.

2011-04-13 11:19:42 補充：
thus, pyridine is much stronger than pyrrole in basicity.