Is phosphorine (C₅H₅P) aromatic?











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Phophorine seems aromatic as it has 6 conjugated electrons. But the answer given is that it is not. This seems odd since pyridine has a similar structure and is also aromatic. Thus I ask is phospohrine aromatic or not?



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aromatic-compounds theoretical-chemistry aromaticity organophosphorus-compounds







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    Phosphinine is aromatic, but somewhat less than benzene.
    – mykhal
    yesterday















up vote
9
down vote

favorite












Phophorine seems aromatic as it has 6 conjugated electrons. But the answer given is that it is not. This seems odd since pyridine has a similar structure and is also aromatic. Thus I ask is phospohrine aromatic or not?



enter image description here






aromatic-compounds theoretical-chemistry aromaticity organophosphorus-compounds







share|improve this question









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user137644 is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
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  • 2




    Phosphinine is aromatic, but somewhat less than benzene.
    – mykhal
    yesterday













up vote
9
down vote

favorite









up vote
9
down vote

favorite











Phophorine seems aromatic as it has 6 conjugated electrons. But the answer given is that it is not. This seems odd since pyridine has a similar structure and is also aromatic. Thus I ask is phospohrine aromatic or not?



enter image description here






aromatic-compounds theoretical-chemistry aromaticity organophosphorus-compounds







share|improve this question









New contributor




user137644 is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.











Phophorine seems aromatic as it has 6 conjugated electrons. But the answer given is that it is not. This seems odd since pyridine has a similar structure and is also aromatic. Thus I ask is phospohrine aromatic or not?



enter image description here






aromatic-compounds theoretical-chemistry aromaticity organophosphorus-compounds




aromatic-compounds theoretical-chemistry aromaticity organophosphorus-compounds






share|improve this question









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user137644 is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.











share|improve this question









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edited 9 hours ago









Mithoron

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3,65082844






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asked yesterday









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  • 2




    Phosphinine is aromatic, but somewhat less than benzene.
    – mykhal
    yesterday














  • 2




    Phosphinine is aromatic, but somewhat less than benzene.
    – mykhal
    yesterday








2




2




Phosphinine is aromatic, but somewhat less than benzene.
– mykhal
yesterday




Phosphinine is aromatic, but somewhat less than benzene.
– mykhal
yesterday










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Phosphorine (IUPAC: phosphinine) actually has aromatic character nearly as great (88%) as that of benzene. According to the reference, phosphorine is sufficiently stable to be handled without air-free techniques; and it undergoes electrophilic substitution reactions similar to those of benzene.






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    Phosphorine (IUPAC: phosphinine) actually has aromatic character nearly as great (88%) as that of benzene. According to the reference, phosphorine is sufficiently stable to be handled without air-free techniques; and it undergoes electrophilic substitution reactions similar to those of benzene.






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      up vote
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      Phosphorine (IUPAC: phosphinine) actually has aromatic character nearly as great (88%) as that of benzene. According to the reference, phosphorine is sufficiently stable to be handled without air-free techniques; and it undergoes electrophilic substitution reactions similar to those of benzene.






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        up vote
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        up vote
        13
        down vote









        Phosphorine (IUPAC: phosphinine) actually has aromatic character nearly as great (88%) as that of benzene. According to the reference, phosphorine is sufficiently stable to be handled without air-free techniques; and it undergoes electrophilic substitution reactions similar to those of benzene.






        share|improve this answer














        Phosphorine (IUPAC: phosphinine) actually has aromatic character nearly as great (88%) as that of benzene. According to the reference, phosphorine is sufficiently stable to be handled without air-free techniques; and it undergoes electrophilic substitution reactions similar to those of benzene.







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        edited 8 hours ago









        Waylander

        5,1221719




        5,1221719










        answered yesterday









        Oscar Lanzi

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        14.1k12446






















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