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- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_II_(Morsch_et_al.)/15%3A_Benzene_and_Aromaticity/15.05%3A_Aromatic_Heterocycles_-_Pyridine_and_PyrroleThe lone pair electrons on pyridine's nitrogen are contained in a sp 2 orbital that lies in the same plane as the ring and does not overlap with the p orbitals of the ring. When looking at the electro...The lone pair electrons on pyridine's nitrogen are contained in a sp 2 orbital that lies in the same plane as the ring and does not overlap with the p orbitals of the ring. When looking at the electrostatic potential map of imidazole, the lone pair electrons on the pyrrole-like nitrogen are distributed around the ring while the lone pair electrons on the pyridine-like nitrogen are non-conjugated and locked into place.
- https://chem.libretexts.org/Courses/Alma_College/Organic_Chemistry_I_(Alma_College)/02%3A_Conjugation_Resonance_and_Aromaticity/2.09%3A_Aromatic_Heterocycles_-_Pyridine_and_PyrroleThe lone pair electrons on pyridine's nitrogen are contained in a sp 2 orbital that lies in the same plane as the ring and does not overlap with the p orbitals of the ring. When looking at the electro...The lone pair electrons on pyridine's nitrogen are contained in a sp 2 orbital that lies in the same plane as the ring and does not overlap with the p orbitals of the ring. When looking at the electrostatic potential map of imidazole, the lone pair electrons on the pyrrole-like nitrogen are distributed around the ring while the lone pair electrons on the pyridine-like nitrogen are non-conjugated and locked into place.
- https://chem.libretexts.org/Courses/Smith_College/Organic_Chemistry_(LibreTexts)/15%3A_Benzene_and_Aromaticity/15.06%3A_Aromatic_Heterocycles_-_Pyridine_and_PyrroleThe lone pair electrons on pyridine's nitrogen are contained in a sp 2 orbital that lies in the same plane as the ring and does not overlap with the p orbitals of the ring. When looking at the electro...The lone pair electrons on pyridine's nitrogen are contained in a sp 2 orbital that lies in the same plane as the ring and does not overlap with the p orbitals of the ring. When looking at the electrostatic potential map of imidazole, the lone pair electrons on the pyrrole-like nitrogen are distributed around the ring while the lone pair electrons on the pyridine-like nitrogen are non-conjugated and locked into place.
- https://chem.libretexts.org/Courses/University_of_Connecticut/Chem_2444%3A_(Second_Semester_Organic_Chemistry)_UConn/03%3A_Conjugated_Pi-Systems_and_Aromaticity/3.08%3A_Aromatic_Heterocycles-_Pyridine_and_PyrroleThe lone pair electrons on pyridine's nitrogen are contained in a sp 2 orbital that lies in the same plane as the ring and does not overlap with the p orbitals of the ring. When looking at the electro...The lone pair electrons on pyridine's nitrogen are contained in a sp 2 orbital that lies in the same plane as the ring and does not overlap with the p orbitals of the ring. When looking at the electrostatic potential map of imidazole, the lone pair electrons on the pyrrole-like nitrogen are distributed around the ring while the lone pair electrons on the pyridine-like nitrogen are non-conjugated and locked into place.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_(OpenStax)/15%3A_Benzene_and_Aromaticity/15.05%3A_Aromatic_Heterocycles_-_Pyridine_and_PyrroleThe definition of aromaticity discussed previously was a cyclic, conjugated molecule containing 4n + 2 π electrons. Nothing in this definition says that the atoms in the ring must be carbon. In fac...The definition of aromaticity discussed previously was a cyclic, conjugated molecule containing 4n + 2 π electrons. Nothing in this definition says that the atoms in the ring must be carbon. In fact, heterocyclic compounds can also be aromatic. A heterocycle is a cyclic compound that contains atoms of more than one element in its ring, usually carbon along with nitrogen, oxygen, or sulfur.
- https://chem.libretexts.org/Courses/SUNY_Oneonta/Organic_Chemistry_with_a_Biological_Emphasis_(SUNY_Oneonta)/07%3A_Acid-base_Reactions/7.06%3A_Acid-base_properties_of_nitrogen-containing_functional_groupsMany of the acid-base reactions we will see throughout our study of biological organic chemistry involve functional groups which contain nitrogen. In general, a nitrogen atom with three bonds and a lo...Many of the acid-base reactions we will see throughout our study of biological organic chemistry involve functional groups which contain nitrogen. In general, a nitrogen atom with three bonds and a lone pair of electrons can potentially act as a proton-acceptor (a base) - but basicity is reduced if the lone pair electrons are stabilized somehow.
- https://chem.libretexts.org/Workbench/Pick_Your_Poison%3A_Introduction_to_Materials_Toxicology/23%3A_Benzene_and_Aromaticity/23.06%3A_Aromatic_Heterocycles_-_Pyridine_and_PyrroleThe definition of aromaticity discussed previously was a cyclic, conjugated molecule containing 4n + 2 π electrons. Nothing in this definition says that the atoms in the ring must be carbon. In fac...The definition of aromaticity discussed previously was a cyclic, conjugated molecule containing 4n + 2 π electrons. Nothing in this definition says that the atoms in the ring must be carbon. In fact, heterocyclic compounds can also be aromatic. A heterocycle is a cyclic compound that contains atoms of more than one element in its ring, usually carbon along with nitrogen, oxygen, or sulfur.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg)/07%3A_Acid-base_Reactions/7.06%3A_Acid-base_properties_of_nitrogen-containing_functional_groupsMany of the acid-base reactions we will see throughout our study of biological organic chemistry involve functional groups which contain nitrogen. In general, a nitrogen atom with three bonds and a lo...Many of the acid-base reactions we will see throughout our study of biological organic chemistry involve functional groups which contain nitrogen. In general, a nitrogen atom with three bonds and a lone pair of electrons can potentially act as a proton-acceptor (a base) - but basicity is reduced if the lone pair electrons are stabilized somehow.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_(Morsch_et_al.)/15%3A_Benzene_and_Aromaticity/15.05%3A_Aromatic_Heterocycles_-_Pyridine_and_PyrroleThe lone pair electrons on pyridine's nitrogen are contained in a sp 2 orbital that lies in the same plane as the ring and does not overlap with the p orbitals of the ring. When looking at the electro...The lone pair electrons on pyridine's nitrogen are contained in a sp 2 orbital that lies in the same plane as the ring and does not overlap with the p orbitals of the ring. When looking at the electrostatic potential map of imidazole, the lone pair electrons on the pyrrole-like nitrogen are distributed around the ring while the lone pair electrons on the pyridine-like nitrogen are non-conjugated and locked into place.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_(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.
- https://chem.libretexts.org/Courses/Oregon_Institute_of_Technology/OIT%3A_CHE_333_-_Organic_Chemistry_III_(Lund)/New_Page/7%3A_Acid-base_Reactions/7.5%3A_Acid-base_properties_of_nitrogen-containing_functional_groupsMany of the acid-base reactions we will see throughout our study of biological organic chemistry involve functional groups which contain nitrogen. In general, a nitrogen atom with three bonds and a lo...Many of the acid-base reactions we will see throughout our study of biological organic chemistry involve functional groups which contain nitrogen. In general, a nitrogen atom with three bonds and a lone pair of electrons can potentially act as a proton-acceptor (a base) - but basicity is reduced if the lone pair electrons are stabilized somehow.
