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- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_(OpenStax)/24%3A_Amines_and_Heterocycles/24.09%3A_Heterocyclic_AminesThis section covers heterocyclic amines, which are organic compounds featuring nitrogen atoms within a ring structure. It discusses their diverse structures, reactivity, and biological importance, suc...This section covers heterocyclic amines, which are organic compounds featuring nitrogen atoms within a ring structure. It discusses their diverse structures, reactivity, and biological importance, such as the roles of pyridine, pyrrole, and imidazole. These heterocyclic amines are significant in pharmaceuticals, agrochemicals, and as biomolecules like nucleic acids. The section also highlights their synthesis and reactions.
- https://chem.libretexts.org/Courses/University_of_Connecticut/Chem_2444%3A_(Second_Semester_Organic_Chemistry)_UConn/11%3A_Chemistry_of_Amines/11.07%3A_Heterocyclic_AminesBecause the nitrogen lone pair is part of the aromatic sextet, the electrons are very stable and are much less available for bonding to a proton (and if they do pick up a proton, the aromatic system i...Because the nitrogen lone pair is part of the aromatic sextet, the electrons are very stable and are much less available for bonding to a proton (and if they do pick up a proton, the aromatic system is destroyed). In the bonding picture for pyridine, the nitrogen is sp 2 -hybridized, with two of the three sp 2 orbitals forming sigma overlaps with the sp 2 orbitals of neighboring carbon atoms, and the third nitrogen sp 2 orbital containing the lone pair.
- https://chem.libretexts.org/Courses/can/CHEM_232_-_Organic_Chemistry_II_(Puenzo)/10%3A_Amines_and_Heterocycles/10.10%3A_Heterocyclic_AminesBecause the nitrogen lone pair is part of the aromatic sextet, the electrons are very stable and are much less available for bonding to a proton (and if they do pick up a proton, the aromatic system i...Because the nitrogen lone pair is part of the aromatic sextet, the electrons are very stable and are much less available for bonding to a proton (and if they do pick up a proton, the aromatic system is destroyed). In the bonding picture for pyridine, the nitrogen is sp 2 -hybridized, with two of the three sp 2 orbitals forming sigma overlaps with the sp 2 orbitals of neighboring carbon atoms, and the third nitrogen sp 2 orbital containing the lone pair.
- https://chem.libretexts.org/Workbench/LCDS_Organic_Chemistry_OER_Textbook_-_Todd_Trout/24%3A_Amines_and_Heterocycles/24.10%3A_Heterocyclic_AminesThe five carbon atoms and the sp 2 -hybridized nitrogen atom each contribute one π electron to the aromatic sextet, and the lone-pair electrons occupy an sp 2 orbital in the plane of the ring (Section...The five carbon atoms and the sp 2 -hybridized nitrogen atom each contribute one π electron to the aromatic sextet, and the lone-pair electrons occupy an sp 2 orbital in the plane of the ring (Section 15.5). The diminished basicity of pyridine compared with that of alkylamines is due to the fact that the lone-pair electrons on the pyridine nitrogen are in an sp 2 orbital, while those on an alkylamine nitrogen are in an sp 3 orbital.
- https://chem.libretexts.org/Courses/Smith_College/Organic_Chemistry_(LibreTexts)/24%3A_Amines_and_Heterocycles/24.10%3A_Heterocyclic_AminesBecause the nitrogen lone pair is part of the aromatic sextet, the electrons are very stable and are much less available for bonding to a proton (and if they do pick up a proton, the aromatic system i...Because the nitrogen lone pair is part of the aromatic sextet, the electrons are very stable and are much less available for bonding to a proton (and if they do pick up a proton, the aromatic system is destroyed). In the bonding picture for pyridine, the nitrogen is sp 2 -hybridized, with two of the three sp 2 orbitals forming sigma overlaps with the sp 2 orbitals of neighboring carbon atoms, and the third nitrogen sp 2 orbital containing the lone pair.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_III_(Morsch_et_al.)/24%3A_Amines_and_Heterocycles/24.09%3A_Heterocyclic_AminesBecause the nitrogen lone pair is part of the aromatic sextet, the electrons are very stable and are much less available for bonding to a proton (and if they do pick up a proton, the aromatic system i...Because the nitrogen lone pair is part of the aromatic sextet, the electrons are very stable and are much less available for bonding to a proton (and if they do pick up a proton, the aromatic system is destroyed). In the bonding picture for pyridine, the nitrogen is sp 2 -hybridized, with two of the three sp 2 orbitals forming sigma overlaps with the sp 2 orbitals of neighboring carbon atoms, and the third nitrogen sp 2 orbital containing the lone pair.
