Dynamic covalent and noncovalent assembly of o-nitrosocumene in organic solvents and water†
Cory H.
Rogers, 
a
Anu
Pradeep,
b
Layla A.
Galiano,
a
S. Ariel
Kelley,
a
Ramkumar
Varadharajan,
b
Ken
Belmore,
a
Logan M.
Whitt,
a
Yanmei
Li,
c
Pier Alexandre
Champagne,
c
Vaidhyanathan
Ramamurthy
*b
and
Silas C.
Blackstock
*a
a
Anu
Pradeep,
b
Layla A.
Galiano,
a
S. Ariel
Kelley,
a
Ramkumar
Varadharajan,
b
Ken
Belmore,
a
Logan M.
Whitt,
a
Yanmei
Li,
c
Pier Alexandre
Champagne,
c
Vaidhyanathan
Ramamurthy
*b
and
Silas C.
Blackstock
*a
Abstract
ortho-Nitrosocumene (o-NC) exhibits dynamic N,N bonding, interchanging monomer and E/Z-azodioxide dimer structures, the extent of which depends on the environment. As a solid, o-NC is a Z-dimer; in organic solvent, the monomer is favored; and in water, dimers are favored. A supramolecular assembly of o-NC is observed as a separate species by NMR in water, shown to be a novel nanometer-sized aggregate containing ∼2000 molecules.
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