Synthesis of a “Masked” Terminal Zinc Sulfide and Its Reactivity with Br?nsted and Lewis Acids

Article abstract of DOI:10.1002/anie.202002364

The “masked” terminal Zn sulfide, [K(2.2.2-cryptand)][^MeLZn(S)] (2) (^MeL={(2,6-ⁱPr₂C₆H₃)NC(Me)}₂CH), was isolated via reaction of [^MeLZnSCPh₃] (1) with 2.3 equivalents of KC₈ in THF, in the presence of 2.2.2-cryptand, at ?78 °C. Complex 2 reacts readily with PhCCH and N₂O to form [K(2.2.2-cryptand)][^MeLZn(SH)(CCPh)] (4) and [K(2.2.2-cryptand)][^MeLZn(SNNO)] (5), respectively, displaying both Br?nsted and Lewis basicity. In addition, the electronic structure of 2 was examined computationally and compared with the previously reported Ni congener, [K(2.2.2-cryptand)][^tBuLNi(S)] (^tBuL={(2,6-ⁱPr₂C₆H₃)NC(^tBu)}₂CH).

Full text of DOI:10.1002/anie.202002364

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Accepted Article
Title: Synthesis of a “Masked” Terminal Zinc Sulfide and its Reactivity
with Brønsted and Lewis Acids
Authors: Miguel Baeza Cinco, Guang Wu, Nikolas Kaltsoyannis, and
Trevor Hayton
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To be cited as: Angew. Chem. Int. Ed. 10.1002/anie.202002364
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10.1002/anie.202002364
Angewandte Chemie International Edition
RESEARCH ARTICLE
Synthesis of a “Masked” Terminal Zinc Sulfide and its Reactivity
with Brønsted and Lewis Acids
Miguel Á. Baeza Cinco,[a] Guang Wu,[a] Nikolas Kaltsoyannis*[b] and Trevor W. Hayton*[a]
Abstract: The “masked“ terminal Zn sulfide, [K(2.2.2-
cryptand][MeLZn(S)] (2) MeL {(2,6-iPr2C6H3)NC(CH3)}2CH), was
mulitple bonds, and we have used this approach to successfully
synthesize a series of terminal actinide chalcogenides, [K(18-
crown-6)][An(E)(NR2)3] (An = Th, U; E = O, S; R = SiMe3), as well
as the aforementioned Ni sulfides.[14,18,19]
Going forward, we were interested in understanding the
extent of  bonding within the [Ni=
S]– fragment. In this regard, the
(
=
isolated via reaction of [MeLZnSCPh3] (1) with 2.3 equiv of KC8 in THF,
in the presence of 2.2.2-cryptand, at –78 °C. Complex 2 reacts readily
with PhCCH and N2O to form [K(2.2.2-cryptand)][MeLZn(SH)(CCPh)]
(4) and [K(2.2.2-cryptand)][MeLZn(SNNO)] (5), respectively, displaying
both Brønsted and Lewis basicity. In addition, the electronic structure
of 2 was examined computationally and compared with the previously
reported Ni congener, [K(2.2.2-cryptand)][tBuLNi(S)] (tBuL = {(2,6-
iPr2C6H3)NC(tBu)}2CH).
isostructural zinc sulfide, which features a closed shell d10 metal
ion, offers a useful comparison with the Ni analogue, because of
its inability to engage in  bonding. Herein, we report the
successful synthesis and structural characterization of a “masked”
terminal Zn sulfide via reductive deprotection, as well as a
preliminary reactivity profile. Moreover, in an effort to better
understand these systems, the [Zn–S]– fragment was probed by
Introduction
DFT/NBO/QTAIM analysis and compared with the [Ni=
S]–
fragment in [K(2.2.2-cryptand)][tBuLNi(S)], as well as the isolated
anion [tBuLNi(S)]–.
Transition metal oxo complexes have been the subject of intense
scrutiny over the past four decades owing to their intermediacy in
a wide array of processes, from biological to industrial.[1–6] Despite
these efforts, the isolation of late metal (i.e., beyond group 8)
terminal oxos has proven challenging  a consequence of the
“oxo wall”.[7] This concept postulates that a terminal oxo in a
tetragonal field with a >d5 configuration will not be isolable
Results and Discussion
Addition of 1 equiv of KSCPh3 to [MeLZnCl][20] in THF results in the
formation of [MeLZn(SCPh3)] (1), which can be isolated in 85 %
yield after work-up (Scheme 1). In the solid state, 1 crystallizes
with two independent molecules in the asymmetric unit (Figure
S21) and its metrical parameters mirror those found in the closely
because of the occupation of M=O * molecular orbitals. In line
with this premise, all known late metal oxo/imido/nitrido
complexes feature reduced coordination numbers, which
liberates d orbitals to host non-bonding electrons. Examples
include Wilkinson’s four-coordinate Ir oxo [Mes3Ir(O)] (Mes =
2,4,6-Me3C6H2),[8] a four-coordinate Co oxo [PhB(tBuIm)3Co(O)]
related Zn trityl thiolate,
[
Me*LZn(SCPh3)]
(
Me*L
= {(2,6-
(CH3)2C6H3)NC(CH3)}2CH), reported by Warren and co-
workers.[21] For instance, the Zn–S distances in 1 are 2.212(3) and
2.191(3) Å, whereas this distance in [Me*LZn(SCPh3)] is 2.2142(6)
Å. In addition, complex 1 has been characterized by 1H and
13C{1H} NMR spectroscopies and elemental analysis. It is stable
(tBuIm
=
3-tBu-imidazolyl),[9] and more recently the four-
coordinate Ir oxo [(PNP)Ir(O)] (PNP = N(CHCHPtBu2)2),[10] among
others.[11–13]
A similar electronic picture arises for the heavier sulfur
congeners. Indeed, the only isolated examples, a family of
“masked”
Ni
sulfides
[K(L)][RLNi(S)]
(RL
=
{(2,6-
iPr2C6H3)NC(R)}2CH; R = Me, tBu; L = 18-crown-6, 2.2.2-
cryptand) reported by our group, all feature trigonal coordination
environments at Ni.[14] These complexes contain a highly reactive
[Ni=
S]– fragment, which can activate a wide variety of small
molecules, including N2O, NO, CO, CS2, and CO2.[14–17] We
accessed these Ni sulfide complexes via reductive removal of a
trityl protecting group. In fact, this “reductive deprotection”
reaction has proven to be broadly useful for the synthesis of M=E
[a]
[b]
M. A. Baeza Cinco, Dr. G. Wu, Prof. Dr. T. W. Hayton
Department of Chemistry and Biochemistry
University of California, Santa Barbara
Santa Barbara, CA 93016 (USA)
E-mail: hayton@chem.ucsb.edu
Prof. Dr. N. Kaltsoyannis
Department of Chemistry
University of Manchester
Oxford Road
Manchester M13 9PL (UK)
E-mail: nikolas.kaltsoyannis@manchester.ac.uk
Supporting information for this article is given via a link at the end of
the document.
Scheme 1. Synthesis of complexes 1 and 2.
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10.1002/anie.202002364
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RESEARCH ARTICLE
for months when stored as a solid under an inert atmosphere at –
24 °C.
ligand in 2. That said, the SꞏꞏꞏK interaction in 2 is still quite long,
suggesting that it can also be considered a “masked” terminal
sulfide.
Next, we applied the reductive deprotection methodology to
1, in an attempt to synthesize a terminal Zn sulfide via selective
C–S bond cleavage. Thus, addition of 2.3 equiv of KC8 to 1 in the
presence of 2.2.2-cryptand in THF at –78 °C results in immediate
formation of a deep red suspension, signalling release of the trityl
anion, [K(2.2.2-cryptand)][CPh3]. Work-up of the reaction mixture
after 10 min enables the isolation of [K(2.2.2-cryptand][MeLZn(S)]
(2), which can be isolated as a yellow crystalline solid in 47% yield
(Scheme 1). Complex 2 has been characterized by X-ray
crystallography, 1H and 13C{1H} NMR spectroscopies, IR and UV-
vis spectroscopies, and elemental analysis. Its crystallizes in the
non-centrosymmetric space group Cc as the Et2O solvate, 2Et2O,
with four independent molecules in the asymmetric unit (Figure 1).
The metrical parameters of all four molecules are similar, and only
the average values will be discussed. The solid-state structure of
2 features a trigonal planar geometry around the Zn center (L-
Table 1. Selected bond lengths and bond angles for the masked sulfides 2

Et2O
and [K(2.2.2-cryptand)][tBuLNi(S)]. Average values shown for 2
(DFT) data in italics. For M–S, the second italicized number refers to the
distance in the isolated anions [RLM(S)]– (R = Me, M = Zn; R = tBu, M = Ni).

Et2O. Computed
Bond/angle
M–S (Å)
2Et2O
[K(2.2.2-cryptand)][tBuLNi(S)]
2.084(1) 2.095, 2.060
3.379(1) 3.349
2.107 2.138, 2.109
3.115 3.223
1.98 2.004
SꞏꞏꞏK (Å)
av. M–N (Å)
M–S–K (°)
1.93 1.973
169.45 176.4
170.08(5) 177.1
Complex 2 is soluble in benzene, toluene, Et2O, DME, THF,
and pyridine, but insoluble in hexanes and pentane. Although 2
can be isolated in analytically pure form and has been fully
characterized, it is relatively unstable. For example, THF solutions
of 2 completely decompose over the course of 3 d, depositing a
colourless solid. An X-ray crystallographic analysis identified the
main decomposition product as the tetrametallic zinc sulfide,
[K(2.2.2-cryptand)]2[MeLZn(µ-S)(µ3-S)Zn]2
(32THF),
which
features a “ladder-like” Zn4S4 core formed by oligomerization of 4
equiv of 2, concomitant with apparent release of 2 equiv of
[K(2.2.2-cryptand)][MeL] (See SI). For comparison, [K(2.2.2-
cryptand)][tBuLNi(S)] features much higher thermal stability,
suggesting that the sulfide ligand in 2 is more reactive, as
anticipated.
To better understand the bonding within the [M–S]– fragment
(M = Zn, Ni) we turned to hybrid density functional theory (PBE0).
We examined the masked platforms
2
and [K(2.2.2-
cryptand][tBuLNi(S)], as well as their isolated anionic components,
i.e., [RLM(S)]– (R = Me, M = Zn; R = tBu, M = Ni). The computed
electronic structures were studied using the Natural Bond Orbital
(NBO) and Quantum Theory of Atoms-in-Molecules (QTAIM)
approaches. Natural atomic charges and M–S Wiberg Bond
Indices (WBIs) are collected in Table 2, and details of the M–S
Natural Localized Molecular Orbitals (NLMOs) are given in Table
S1 and Figures S1-S12. Note that both the isolated and masked
anions for the Ni analogue were calculated in their triplet state (the
lowest singlet state of the isolated anion was found to be 51.2
kJ/mol less stable than the triplet, and the electronic structure of
the quintet failed to converge). Minimal spin contamination was
found in both Ni systems, with <S2> = 2.03 for [tBuLNi(S)]– and 2.02
for [K(2.2.2-cryptand][tBuLNi(S)].
Figure 1. Molecular structure of 2Et2O. Thermal ellipsoids shown at 50%
probability. Et2O solvates, hydrogen atoms, and three other molecules in the
asymmetric unit omitted for clarity.
Zn-L = 359.8), as well as a remarkably short av. Zn–S bond
length of 2.107 Å (range: 2.083(5)–2.148(5) Å). We ascribe this
short distance to the electrostatic contraction originating from the
high charge on the S atom. For comparison, the bridging Zn
sulfide complex, [{HB(3-p-cumenyl-5-methylpyrazolyl)3}Zn]2(µ–
S),[22] has a Zn–S bond length of 2.186(2) Å, while the two-
coordinate Zn dithiolate complex, [(2,6-iPr2C6H3)S]2Zn,[23] has a
Zn–S distance of 2.1596(6) Å.
A
comparison of 2 with its Ni analogue, [K(2.2.2-
cryptand)][tBuLNi(S)] is also informative (Table 1). Surprisingly, its
M–S bond length (2.084(1) Å) is comparable to those of 2, despite
the nominally higher bond order in the Ni example. However,
complex 2 possesses a shorter average SꞏꞏꞏK distance (3.115 Å)
than that observed for [K(2.2.2-cryptand)][tBuLNi(S)] (3.379(1) Å),
consistent with the higher predicted charge density at the S2-
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10.1002/anie.202002364
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RESEARCH ARTICLE
Both the isolated anion, [MeLZn(S)]–, and 2 have a single Zn–
S  bonding NLMO, which is mainly S3p in character. The
remaining two S3p orbitals correspond to the sulfur lone pairs.
These orbitals do not interact with the Zn center, consistent with
the 3d10 configuration of Zn2+ (Figure 2). Additionally, 2 features a
somewhat smaller Zn–S WBI than in the isolated anion, reflecting
its slightly longer bond length (Table 1). This is also the case for
the QTAIM delocalisation indices (Table 2), although the absolute
values of these bond order measures are significantly larger than
the analogous WBIs. For both Zn–S bonds, the QTAIM ellipticities
at the bond critical point are very close to zero (Table 2), as
expected for a cylindrically symmetrical interaction, and are
consistent with a formal bond order of 1.
As noted above, the experimental SꞏꞏꞏK distance is
significantly longer in [K(2.2.2-cryptand)][tBuLNi(S)] than in 2,
attributed to higher charge density at S. The difference in the
calculated SꞏꞏꞏK distances between the two masked systems is
not as large as seen experimentally, but that in the Ni complex is
0.126 Å longer than in 2 (Table 1). Finally, Table 2 shows that the
Natural charge of the S atom is indeed more negative in 2 than in
[K(2.2.2-cryptand)][tBuLNi(S)], which may account for its greater
reactivity.
We next explored the reactivity of 2 towards electrophiles.
Reaction of 2 with 1 equiv of PhCCH in toluene resulted in
formation of a new Cs-symmetric product, as revealed by 1H NMR
spectroscopic monitoring of the reaction. Work-up of the reaction
mixture
resulted
in
isolation
of
[K(2.2.2-
cryptand)][MeLZn(SH)(CCPh)] (4), which was formed by
protonation of the Zn–S bond of 2 by PhCCH (Scheme 2).
Complex 4 can be isolated as large colorless plates in 41 % yield
as the THF solvate, 42THF. This reaction clearly illustrates the
potent basicity of 2, especially relative to [K(18-crown-
6)][tBuLNi(S)], which does not react with PhCCH.
Complex 42THF crystallizes in the monoclinic space group
P21/n (Figure 3). In the solid state, the Zn ion adopts a pseudo-
tetrahedral geometry (τ4 = 0.928),[24] and is bound by a -
diketiminate ligand, a hydrosulfide ligand, and a phenylacetylide
ligand. The structure also possesses an outer sphere [K(2.2.2-
cryptand)]+ cation. The Zn–S bond length (2.332(3) Å) is
substantially longer than the Zn–S distance observed in 2, as
expected. The Zn–C distance in 4 (2.021(5) Å) is similar to that in
other Zn acetylide complexes, such as α-diimine-supported
Figure 2. Comparison the S3p orbital (NLMO 56) in [MeLZn(S)]– vs. the Ni–S

 orbital (NLMO 155) in [tBuLNi(S)]–. Isosurface value = 0.05. Hydrogen atoms
omitted for clarity.
In [tBuLNi(S)]–, there are five  spin and three  spin Ni
3d-based orbitals, as expected for a Ni2+ d8 configuration. There
is also an  spin NiS  NLMO which is similar in composition to
the Zn equivalent, although the metal component, which is
predominantly s in character, is reduced in the Ni system (14.2%
vs 21.5% for Zn). There is a  spin equivalent of this NLMO. In
addition, there are two  spin Ni–S  NLMOs, which have more
metal content (40.0% and 24.7%) than the  orbitals and are
Ni3d/S3p in character (Figure 2). The Ni–S WBI and values are
both significantly larger than in [MeLZn(S)]–, reflecting the 
bonding in the Ni system and a formal M–S bond order of 2. The
presence of two orthogonal  spin  orbitals accounts for the bond
critical point ellipticity remaining close to zero. The Ni–S bonding
in [K(2.2.2-cryptand)][tBuLNi(S)] is similar: one  spin  NLMO,
and + 2 in the  spin manifold. The NLMOs are generally more
S-localised in [K(2.2.2-cryptand)][tBuLNi(S)] than the anion alone,
as a result of the slightly longer M–S bond, and the WBI and  are
smaller, as in the Zn systems.
[LZn(CCPh)2] (Zn–C
iPr2C6H3)NC(CH3)}2),
=
1.966(3), 1.953(3) Å) (L
and the homoleptic
=
{(2,6-
acetylide,
K2[Zn(CCPh)4] (av. Zn–C = 2.0475 Å).[25] The 1H NMR spectrum
of 4 is consistent with the Cs symmetry observed in the solid state;
i
for instance, its 1H NMR spectrum shows two inequivalent Pr
environments. In addition, the hydrosulfide S–H resonance was
observed at  = -2.45 ppm, further confirming our formulation.
This value is similar to those of other Zn hydrosulfides.[22,26,27]
Finally, we observe the CC mode in 4 at 2096 cm-1 (Figure S27).
Table 2. Natural atomic charges q, M
delocalisation indices , and ellipticities at the M
MeLZn(S)]–, [K(2.2.2-cryptand)][MeLZn(S)] (2),
cryptand)][tBuLNi(S)].
–
S Wiberg Bond Indices WBI, M
S bond critical point  for
tBuLNi(S)]– and [K(2.2.2-
–
S
–

[
[
qM
qS
WBI
0.68
0.51


[
MeLZn(S)]–
1.38
1.48
-1.45
-1.52
1.20
1.03
0.01
0.02
[K(2.2.2-
cryptand)][MeLZn(S)] (2)
Scheme 2. Synthesis of complexes 4 and 5.
[
tBuLNi(S)]–
0.88
1.04
-1.04
-1.22
1.18
0.95
1.57
1.34
0.04
0.02
Exposure of complex 2 to 1 atm of N2O results in rapid
formation
of
the
thiohyponitrite
complex,
[K(2.2.2-
[K(2.2.2-cryptand)][tBuLNi(S)]
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10.1002/anie.202002364
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RESEARCH ARTICLE
1
cryptand)][MeLZn(SNNO)] (5) (Scheme 2), which can be isolated
as a colorless crystalline solid in 54 % yield. Complex 5 is only the
second example of a thiohyponitrite complex, the first being
formed from the analogous reaction of N2O with [K(18-crown-
6)][tBuLNi(S)].[14] It is worth noting that the reaction of complex 2
with N2O reaches completion almost immediately (< 4 min),
whereas the reaction of N2O with the isostructural Ni sulfide
complex requires ca. 3 hr to reach completion. The Zn center in
52.5C6H6 features a distorted tetrahedral geometry (τ4 = 0.773)[24]
that is bound with a 2 cis-thiohyponitrite ligand and the -
diketiminate ligand, displaying overall Cs symmetry (Figure 3).
The O–N and N–N distances in 5 are 1.229(6) Å and 1.306(7) Å,
respectively. Curiously, these values are much different than
those observed for [K(18-crown-6)][tBuLNi(SNNO)]. For example,
the O–N and N–N distances in [K(18-crown-6)][tBuLNi(SNNO)] are
1.308(1) Å and 1.154(9) Å, respectively. Likewise, longer and
shorter O–N and N–N distances, respectively, are found in most
other hyponitrite complexes, including [(PPh3)2Pt(O2N2)] (av. O–
N = 1.37 Å, N–N = 1.23 Å),[28] {[Fe(NO)2]2(μ-bdmap)}2(κ4-N2O2)
(bdmap = 1,3-bis(dimethylamino)-2-propanolate; O–N = 1.330(3)
Å, N–N = 1.279(5) Å),[29] and K2[(NON)Al(η2-O2N2)]2 (NON = 4,5-
The H NMR spectrum of 5 features signals assignable to a
single iPr environment for the -diketiminate ligand (Figure S20),
as evidenced by the diastereotopic methyl resonances at 1.59
and 1.33 ppm. The 1H NMR spectrum of 5 argues for a C2v-
symmetric complex in solution, which contrasts with the Cs
symmetry observed in the solid state. To explain this observation,
we suggest that the thiohyponitrite ligand can adopt a 1 binding
mode, which allows it to rotate within the -diketiminate binding
pocket. We hypothesize that the apparent low barrier of
exchange is due to the additional contribution of the [SNN=
O]2–
resonance form. Further NMR characterization of 5 was
hampered by its poor solubility or instability in most solvents.
Intriguingly, however, when 5 was dissolved in pyridine-d5, it
converted into 3, suggesting that N2O addition to 2 is reversible
under some conditions.
Conclusions
In conclusion, we synthesized and characterized the first “masked”
terminal zinc sulfide, [K(2.2.2-cryptand][MeLZn(S)], via reductive
deprotection of the Zn trityl thiolate complex, [MeLZn(SCPh3)].
[K(2.2.2-cryptand][MeLZn(S)] is among a growing number of
chalcogenide complexes,[41–44] such as the recently isolated
molecular Al oxides K2[(NON)Al(O)(THF)]2 and K2[(ArNON)Al(O)]2
(ArNON = [O(SiMe2NAr)2]2–, Ar = 2,6-iPr2C6H3), as well as the in-
situ generated Ga oxide [MeLGa(O)],[30,34,45] which feature minimal
(if any) M–E -bonding. Indeed, our Natural Localised Molecular
Orbital analysis finds only a Zn–S  bond in both [K(2.2.2-
cryptand][MeLZn(S)] and its anionic fragment, [MeLZn(S)]–. By
contrast, the Ni–S  bonding in the isostructural Ni complex,
[K(2.2.2-cryptand)][tBuLNi(S)], is augmented by two  spin Ni–S 
orbitals. Moreover, our DFT analysis confirms the predicted
stronger polarization within the Zn–S bond, in accordance with
experimental observations. The decrease in bond order on
moving from the Ni to Zn analogue is important confirmation of
the central tenet of the “oxo wall” postulate. Intriguingly, though,
the M–S bond lengths within these two fragments are essentially
identical, despite their fundamentally different bonding schemes
(M–S = 0.023 Å).
bis(2,6-iPr2-anilido)-2,7-tBu2-9,9-dimethylxanthene; av. O-N
=
1.378 Å, N–N = 1.251(3) Å),[30] among others.[31–34] Overall, the
structural features observed for 5, especially the N–N distance,
suggest a contribution of the [SNN
overall electronic structure, in addition to the expected [EN
(E O, S) resonance form observed previously for the
=
O]2– resonance form to the
=
NO]2–
=
(thio)hyponitrite ligand. Complex 5 also possesses Zn–O and Zn–
S distances of 1.977(2) Å and 2.226(2) Å, respectively. These
values fall within the expected range for the Zn2+ ion.[35–40]
Finally, we found that [K(2.2.2-cryptand][MeLZn(S)] can
deprotonate
cryptand)][MeLZn(SH)(CCPh)] and, more remarkably, capture
N2O, forming the thiohyponitrite complex, [K(2.2.2-
PhCCH
to
produce
[K(2.2.2-
cryptand)][MeLZn(SNNO)], which contains a rare example of an
[SNNO]2– ligand. These reactions clearly outline the potent
reactivity of the sulfide ligand in [K(2.2.2-cryptand][MeLZn(S)],
which can function as both a strong Brønsted and Lewis base.
Further reactivity studies with other small molecules are currently
underway.
Acknowledgements
This work was supported by the National Science Foundation
(CHE 1764345). NMR spectra were collected on instruments
supported by an NIH Shared Instrumentation Grant (SIG,
1S10OD012077-01A1). We are grateful to the University of
Figure 3. Molecular structures of 42THF (top) and 52.5C6H6 (bottom). Thermal
ellipsoids shown at 50% probability. Except for the hydrosulfide proton in 4, all
hydrogen atoms omitted for clarity. Solvate molecules and [K(2.2.2-cryptand)]+
cations omitted for clarity.
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RESEARCH ARTICLE
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138, 5008–5011.
[33] S. C. Puiu, T. H. Warren, Organometallics 2003, 22, 3974–
3976.
Keywords: zinc • sulfides • nitrogen oxides • protecting groups •
multiple bonding
[34] M. D. Anker, M. P. Coles, Angew. Chem. Int. Ed. 2019, 58,
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10.1002/anie.202002364
Angewandte Chemie International Edition
RESEARCH ARTICLE
Entry for the Table of Contents
RESEARCH ARTICLE
Miguel Á. Baeza Cinco, Guang Wu,
Nikolas Kaltsoyannis* and Trevor W.
Hayton*
Page No. – Page No.
Synthesis of a “Masked” Terminal
Zinc Sulfide and its Reactivity with
Brønsted and Lewis Acids
The “masked“ terminal Zn sulfide, [K(2.2.2-cryptand][MeLZn(S)] (MeL = {(2,6-
iPr2C6H3)NC(CH3)}2CH), displays high Brønsted and Lewis basicity in its reactions
with phenylacetylene and nitrous oxide, respectively.
This article is protected by copyright. All rights reserved.