In the following orbital the lone pair on each N atom is present:
N1: sp3,
N2: p,
N3: p,
N4: sp2,
N5: sp2
Sitagliptin is an anti-diabetic drug used to treat type 2 diabetes and is marketed under the brand names Januvia and others. One carbon atom has no pi bonds, while the first nitrogen atom is linked to two hydrogen atoms. It thus possesses sp3 hybridization.
The second nitrogen atom possesses a single pair of electrons and is bound to three other atoms. It is hence sp2 hybridized. The nitrogen atoms in positions 3, 4, and 5 have sp2 hybridization.
The lone pair of nitrogen in the first nitrogen atom is in the sp3 orbital. The second and third nitrogen atoms' only pair of electrons are in p-orbitals. The fourth and fifth nitrogen atoms' lone pair of electrons are in sp2 orbitals.
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