Grandberg, I. I. et al. published their research in Khimiya Geterotsiklicheskikh Soedinenii in 1966 | CAS: 4783-68-0

2-Phenoxypyridine (cas: 4783-68-0) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Reference of 4783-68-0

Comparative basicities of substituted pyridines and electronegativity series in pyridines was written by Grandberg, I. I.;Faizova, G. K.;Kost, A. N.. And the article was included in Khimiya Geterotsiklicheskikh Soedinenii in 1966.Reference of 4783-68-0 This article mentions the following:

From a comparison of the pKa values of pyridine and 74 substituted pyridines (I), the effects of substituent groups on basicity were distinguished. For 2-substituents the order of decreasing basicity is: Cl > Br ≥ I > PhO > Ac > MeO > m-O2NC6H4 > p-O2NC6H4 > CHO > 2,4-(O2N)2C6H3CH2 > Ph > CH(OH)Ph > CPh:CH2 > vinyl > H > benzyl > 1-cyclohexen-1-yl ≥ CMe:CH2 > CH2OH > Me2CHCH2 ≥ HOCH2CH2 > iso-Pr ≥ Me. For 3-substituents the corresponding order is: NO2 > Cl > Br > CO2Et > Ac > CHO > CCH > Ph > MeO > vinyl > H > OH > Me ≥ Et ≥ iso-Pr ≥ Me2CHCH2. For 4-substituents the order is: NO2 > Cl > CO2Et > Ac > CCPh > CHO > p-O2NC6H4 > m-O2NC6H4 > CH:CHC6H4NO2-p > H > vinyl > benzyl > Ph > CH:CHC6H4Cl-p > CH:CHPh > CH:CHC6H4Me-p > iso-Bu > CH:CHC6H4Pr-iso-p ≥ Me ≥ Et ≥ iso-Pr ≥ CH:CHC6H4OMe-p > MeO. Some data are given also for pyridine oxides. The results were interpreted in terms of inductive and mesomeric effects. The latter were found to be more important at the 4-position than at the 2-position. Hydroxy substitution in the 3-position showed a pronounced mesomeric effect. Hydroxy substitution in the 2- and 4-positions was not studied because of pyridone tautomerism. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0Reference of 4783-68-0).

2-Phenoxypyridine (cas: 4783-68-0) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Reference of 4783-68-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem