Effect of Hydrogen Binding on Selective Recognition of Halide Anions

Article abstract of DOI:10.1002/cjoc.201600237

The interplay of molecular rigidity enforced by interior or exterior hydrogen bonding and affinity for binding halide anions is described to demonstrate the effect of intramolecular hydrogen bonding in anion recognition process. To this end pyridine-2,6-d

Full text of DOI:10.1002/cjoc.201600237

FULL PAPER
DOI: 10.1002/cjoc.201600237
Effect of Hydrogen Binding on Selective Recognition of
Halide Anions
Juan Du, Kang Kang, Jinchuan Hu, Lijun Mao, Lihua Yuan, and Wen Feng*
Institute of Nuclear Science and Technology, Key Laboratory for Radiation Physics and Technology of Ministry of
Education, College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China
The interplay of molecular rigidity enforced by interior or exterior hydrogen bonding and affinity for binding
halide anions is described to demonstrate the effect of intramolecular hydrogen bonding in anion recognition pro-
cess. To this end pyridine-2,6-dicarboxamides 1 and 2, and aromatic oligoamides 3 and 4 containing intramolecular
hydrogen bonds were explored for their ability in associating with tetrabutylammonium halide (Cl, Br, and I).
1
Binding constants in chloroform solution were calculated using nonlinear curve-fitting method based on H NMR
titration experiments. The trimeric amide 3, which adopts a crescent conformation as revealed by single-crystal
X-ray diffraction analysis, strongly binds chloride anion with binding constant as high as 379 L•mol1. This is more
than 6 times greater than the binding constant for the control receptor 2 with a backbone that is only partially rigidi-
fied. The comparative data provided supportive information for rationalizing the observed affinity difference in
binding halide anions in terms of local preorganization effected by interior or exterior hydrogen bonding.
Keywords hydrogen bonding, halide anion, recognition, selectivity
Introduction
NH protons and preorganization of the scaffolds.[1] For
example, the enhanced binding was achieved by a co-
operative polarization effect induced by intramolecular
coordination of the amide carbonyl to a Lewis acidic
boronate group.[11] Introduction of positive charges as
indicated in dicationic pyridine-2,6-dicarboxamide re-
ceptors also led to improved binding affinity towards
anions.[12] Paricularly, one example by Davis et al. ex-
plored the effect of internal hydrogen bonding of the
amide oxygens to properly positioned hydroxyl
groups.[14] Intramolecular hydrogen bonds were re-
vealed to preorganize isophthalamide, leading to both
increased affinity and selectivity of anion binding for
transmembrane transport of Cl. In fact, incorporation of
hydrogen bonds into ligands was able to orient incom-
ing groups or stabilize metal-ligand adducts.[14] Never-
theless, the relationship between H-bonding and the
resulting behaviour associated with the molecular con-
formation of complexes has remained largely enigmatic
in a specific metal ion-chelating system.
Hydrogen bonding (H-bonding) has been considered
as one of the most important non-covlaent forces in reg-
ulating recogntion, self-assembly and hierachical or-
ganization of natural and synthetic molecules.[1] Of par-
ticular interest is its use in enforcing crescent or helical
conformation on artificial molecules.[2] Such folded
conformation makes it possible to orient functional
groups therein in the preorganized manner, thus provid-
ing demonstrated performance such as metal complexa-
tion,[3] catalysis[4] and separation.[5] Rigid aromatic oli-
goamides including their cyclic counterparts with de-
fined conformation by intramolecualr hydrogen bond-
ing,[2-6] represent a class of shape-persistent compounds
that have exhibited capabilities of binding inorgainc[5] or
organic cations.[7] Importantly, rigification of their
backbones through local conformational preferences
contributes significantly to the observed behaviour.
Amide-based receptors for anion recogniton have
received intensive research interest in the last two dec-
ades.[8-10] The amide hydrogens usually serve as hydro-
gen bonding donor to target specific anions.[11] Among
the most widely investigated constructing units for these
receptors are diamide derivatives of isophthalic and
pyridine-2,6-dicarboxylic acids.[10] To enhance binding
ability, various design strategies were reported, most of
which are associated with increasing acidity of amide
We are interested in using of organic hosts for metal
chelation and sensing as well as separation.[15,16] Partic-
ularly intriguing is the effect of intramolecular H-
bonding-enforced local rigification of molecular struc-
ture upon the complexation behaviour in oligomeric
amide-related compounds. We recently revealed a clear
connection between molecular structures of N-substi-
tuted picolinamides and extraction behaviour based on
*
E-mail: wfeng9510@scu.edu.cn
Received April 19, 2016; accepted May 27, 2016; published online XXXX, 2016.
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/cjoc.201600237 or from the author.
Chin. J. Chem. 2016, XX, 1—7
© 2016 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
1

Du et al.
FULL PAPER
the relationship between intramolecular H-bonding and
rotational isomerism. In addition, insertion of a hydro-
gen-bonded amide spacer into CMPO-calixarenes was
found to implicate a great influence upon selective ex-
traction of f-block elements.[17] Despite the fact that
numerous amide-based receptors have been generated,
the interplay between intramolecular hydrogen bonding
and binding affinity of halide anions is still scarcely
investigated. Furthermore, no efforts have been directed
to comparative study under the same condition using
pyridine-2,6-dicarboxamide with interior H-bonds and
aromatic oligoamides containing exterior hydrogen
bonds.
In this paper we probe and compare the extent to
which the affinity and selectivity can be affected by the
backbone rigidification of these two types of receptors
with interior and exterior H-bonds. With this in mind,
compounds 1－4 (Figure 1) were selected for the anion
recognition in the experiments. Different from the clas-
sical structures documented,[18] pyridine-2,6-dicar-
boxamide 1 contains two highly stable intramolecular
three-center hydrogen bonds. Introduction of propoxy
groups in 1 at ortho-position adjacent to the amide bond
allows formation of these two three-center hydrogen
bonds, which leads to the rigidification of the backbone
of the molecule. Receptor 2, a structural isomer of 1,
was chosen as sterically unconstrained control for 1. Its
molecular skeleton is only partially rigidified due to
depletion of two hydrogen bonds by placing the sub-
stituent at para-position. Aromatic oligoamide 3, an
analogue of well-known amide-based receptors,[19] was
prepared. It contains two intramolecular hydrogen
bonds on the exterior of the molecule, but the two cen-
tral amide bonds could still rotate freely. This is in stark
contrast to shape-persistent trimer 4, whose backbone is
fully rigid via intramolecular hydrogen bonding of
alkoxy groups with the N-H protons.
dissolved in anhydrous CH2Cl2 (20 mL) and added
dropwise to a solution containing oxalyl dichloride (302
mg, 2.38 mmol) and a drop of DMF in CH2Cl2 (10 mL).
The solution was stirred at room temperature under N2
atmosphere for 1 h. Removal of the solvent afforded the
dichloride. Compound 25 (250 mg, 1.19 mmol) was
hydrogenated in the presence of 20% Pd/C (50 mg) in
CH2Cl2 at 0.3 MPa for 10 h. The solution was filtered in
darkness as fast as possible followed by immediate
removal of the solvent. The reduced diamine was used
for the immediate coupling reaction. The dichloride in
CH2Cl2 (50 mL) was added dropwise to a mixture of the
above diamine and Et3N (241 mg, 2.38 mmol) in
anhydrous CH2Cl2 (50 mL). The solution was stirred
under N2 for 7 h. The organic layer was washed with
water (20 mL×3) and dried over anhydrous Na2SO4
and filtered. The crude product was purified by
chromatography on silica gel [V(CH2Cl2)∶V(EA)＝
10∶1] to provide the product 3 as a white solid (204
1
mg, 65.2%). H NMR (400 MHz, CDCl3) δ: 9.65 (s,
2H), 8.34 (s, 2H), 8.04 (s, 2H), 7.89 (q, J＝4.7 Hz, 2H),
7.84 (s, 1H), 7.49 (s, 2H), 6.79 (s, 2H), 3.91 (s, 6H),
3.83 (s, 3H), 2.69 (br s, 6H); 13C NMR (100 MHz,
DMSO-d6, 298 K, containing 5 equiv. of TBACl) δ:
165.18, 164.13, 159.20, 153.11, 135.91, 132.11, 124.18,
122.88, 122.74, 119.25, 116.19, 111.92, 57.49, 55.97,
55.67, 26.37, 23.09, 19.11, 13.39. ESI-HRMS calcd for
C27H28N4O7 [M]+ 520.1958, found [M＋H]＋ 521.2031;
[M＋Na]＋ 543.1842; [M＋K]＋ 559.1575; [M＋Cl]
555.1641.
Binding constant determination
The binding constants for the anion complexation of
2b and 3 in CDCl3 were determined by NMR titration
experiments with keeping the concentration of 2b and 3
as a constant (1.0 mmol/L) and varying the concentra-
tion of tetrabutylammonium chloride (TBACl). The
binding constants were determined by plotting the
chemical shift of proton Hq in 3 versus the concentration
of 3 based on Eq. 1.[20-22]
Experimental
Instruments and materials
1H NMR and 13C NMR spectra were recorded on a
Bruker AVANCE AVⅡ-400 MHz (1H: 400 MHz; 13C:
100 MHz). Chemical shifts are reported with δ values
and coupling constants (J) are denoted in Hz. Multiplic-
ities are denoted as follows: s＝singlet, d＝doublet, t＝
triplet, and m＝multiplet. High resolution mass (HRMS)
data were obtained on a WATERS Q-TOF Premier.
Solvents for extraction and chromatography were rea-
gent grade. CDCl3 was from Cambridge Isotope Labor-
atories (CIL). All chemicals were obtained from com-
mercial suppliers and were used as received unless oth-
erwise noted. CH2Cl2 was dried over CaH2. Column
chromatography was carried out using silica gel (300－
400 mesh).
where δobs is the observed chemical shift of proton Hq;
δb is the chemical shift of proton Hq in complex; δf is the
chemical shift of proton Hq in free 3; [H]0 is the total
concentration of the host; [G]0 is the total concentration
of the guest; Ka is the binding constant.
Results and Discussion
Synthesis of compound 3
Conformational preferences of receptors
5-Methoxyisophthalic acid (117 mg, 0.60 mmol) was
All hydrogen bonded compounds 1－4 were pre-
2
www.cjc.wiley-vch.de
© 2016 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2016, XX, 1—7

Du et al.
FULL PAPER
slightly twisted away from each other. This is partially
ascribed to the involvement of H-bonding with water
molecules. The two amide nitrogen atoms in 3 are sp2
hybridized since the bond angles across each of the two
amide nitrogens N1 and N3 are ca. 129.745(2)° and
126.925(2)°, respectively. The mean deviations of two
amide groups C12-C13-C16-O3-H2-N2 (plane 1) and
C22-C23-C26-O6-H4-N4 (plane 2) are 0.0356 and
0.0744.
periphery of the second receptor, which is stabilized by
three H-bonds: (O10…H10B…O5', O10…H10A…O9,
O9…H8A…O8 and O8…H8B…O5'). The water mole-
cule (H10B－O10－H10A) is considered as a major
non-covalent linking bridge to construct the network
because it interacts with two receptors at the same time.
Any one of the other two water molecules (H8B－O8－
H8A and H11B－O11－H11B) is incapable of forming
H-bonds with two receptors concomitantly. Therefore,
water molecules actually function as crosslinker to form
a continuously packed lattice via intermolecular
H-bonding interactions.
Table 1 Crystal data and structure refinement for 3
Empirical formula
Formula weight
Temperature/K
Crystal system
Space group
a/Å
C54H70N8O21
1167.18
139.95(10)
monoclinic
C2/c
18.4508(5)
10.7065(3)
28.0335(7)
90
b/Å
c/Å
α/(°)
β/(°)
95.447(2)
90
γ/(°)
Volume/Å3
5512.8(2)
4
Z
ρcalc/(mg•mm3)
μ(Mo Kα)/mm1
F(000)
1.406
0.109
2472.0
Crystal size/mm3
0.3×0.2×0.2
2θ range for data collection
5.84° to 52.744°
22≤h≤12
12≤k≤13
35≤l≤32
12237
Index ranges
Reflections collected
Independent reflections
Data/restraints/parameters
Goodness-of-fit on F2
Final R indexes [I≥2σ(I)]
Final R indexes [all data]
5634 [R(int)＝0.0261]
5634/1/411
1.026
R1＝0.0440, wR2＝0.0943
R1＝0.0626, wR2＝0.1055
Largest diff. peak and hole/(e•Å3) 0.21 and 0.26
In the packing diagram (Figure 2b), two water mol-
ecules (produced adventitiously from exposure to the
atmosphere during the crystallization process) perch in
the cleft above the center of the crescent cavity by in-
teracting with 3 through five hydrogen bonds: H3…O10
distance 2.2500(1) Å, N3…H3…O10 angle 162.731(3)°;
H1…O10 distance 2.2788(0) Å, N1…H1…O10 angle
146.735(2)°; H4A…O10 distance 2.3348(0) Å, C4…
H4A …O10 angle 137.256(2)°; H9A …O4 distance
1.8844(0) Å, O9…H9A…O4 angle 163.489(1)°; H9B…
O7 distance 1.8018(0) Å, O9 …H9B …O7 angle
164.301(3)°. The bond lengths are in the range of 1.80
－2.34 Å. The third water molecule is located at the
Figure 2 The crystal structure of 3 (a) single molecule
containing two water molecules; (b) packing diagram of
hydrogen bonding-mediated trimer. Hydrogen atoms are omitted
for the sake of clarity except for those forming hydrogen bonds.
The parameters of some H-bonds in 3 are shown in
Table 2. It is worth noting that the H-bond lengths of
O10－H10A…O9, O8－H8A…O9, and O11－H11A…
O8 are 1.78980(0) Å, 1.9034(0) Å and 1.9341(0) Å,
which are much shorter than those of N1－H…O10 and
N3－H…O10, suggesting the formation of stronger
4
www.cjc.wiley-vch.de
© 2016 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2016, XX, 1—7

Du et al.
FULL PAPER
H-bonding at the two terminal aromatic rings. Con-
sistent with the molecular conformation in which two
adjacent amide hydrogens at the central aromatic moiety
point inwards, 3 demonstrates a binding affinity that is
more than 6 times higher than that for control receptor
2b towards the binding of chloride anion. Despite the
fact that the presence of N in pyridine moiety tends to
increase the acidity of amide proton[8n] in 1 or 2, the
formation of intramolecular H-bonds significantly low-
ers the binding affinity whatever it is from exterior or
interior H-bonds due to the saturation of H-bonding in-
teractions.
Specialized Laboratory, College of Chemistry, Sichuan
University is acknowledged for NMR, HRESI-MS and
IR analyses.
References
[1] (a) Jeffrey, G. A.; Sanger, W. Hydrogen Bonding in Biological
Structures, Springer, Berlin, Heidelberg, 1994; (b) Jeffrey, G. A.
Crystallogr. Rev. 1995, 4, 213; (c) Jeffrey, G. A. An Introduction to
Hydrogen Bonding, Oxford University Press, New York, 1997; (d)
Scheiner, S. Hydrogen Bonding: A Theoretical Perspective, Oxford
University Press, New York, 1997.
[2] (a) Foldamers: Structure, Properties, and Applications, Eds.: Hecht,
S.; Huc, I., Wiley-VCH, Weinheim, 2007; (b) Gong, B. Acc. Chem.
Res. 2008, 41, 1376; (c) Li, Z.-T.; Hou, J.-L.; Li, C. Acc. Chem. Res.
2008, 41, 1343; (d) Zhang, D.-W.; Zhao, X.; Hou, J.-L.; Li, Z.-T.
Chem. Rev. 2012, 112, 5271; (e) Yamato, K.; Kline, M.; Gong, B.
Chem. Commun. 2012, 48, 12142; (f) Fu, H. L.; Liu, Y.; Zeng, H. Q.
Chem. Commun. 2013, 49, 4127; (g) Gong, B.; Shao, Z. F. Acc.
Chem. Res. 2013, 46, 2856; (h) Ong, W. Q.; Zeng, H. J. Incl.
Phenom. Macrocycl. Chem. 2013, 76, 1.
[3] (a) Qin, B.; Ren, C. L.; Ye, R. J.; Sun, C.; Chiad, K.; Chen, X. Y.; Li,
Z.; Xue, F.; Su, H. B.; Chass, G. A.; Zeng, H. Q. J. Am. Chem. Soc.
2010, 132, 9564; (b) Ren, C. L.; Maurizot, V.; Zhao, H. Q.; Shen, J.;
Zhou, F.; Ong, W. Q.; Du, Z. Y.; Zhang, K.; Su, H. B.; Zeng, H. Q. J.
Am. Chem. Soc. 2011, 133, 13930.
[4] Zhao, H. Q.; Shen, J.; Guo, J. J.; Ye, R. J.; Zeng, H. Q. Chem.
Commun. 2013, 49, 2323.
[5] Zhong, L. J.; Chen, L.; Feng, W.; Zou, S. L.; Yang, Y. Y.; Liu, N.;
Yuan, L. H. J. Incl. Phenom. Macrocycl. Chem. 2012, 72, 367.
[6] (a) Gan, Q.; Ferrand, Y.; Bao, C. Y.; Kauffmann, B.; Grélard, A.;
Jiang, H.; Huc, I. Science 2011, 331, 1172; (b) Ferrand, Y.; Gan, Q.;
Kauffmann, B.; Jiang, H; Huc, I. Angew. Chem., Int. Ed. 2011, 50,
7572; (c) Cai, W.; Wang, G.-T.; Xu, Y.-X.; Jiang, X.-K.; Li, Z.-T. J.
Am. Chem. Soc. 2008, 130, 6936; (d) Sun, C.; Ren, C. L.; Wei, Y. C.;
Qin, B.; Zeng, H. Q. Chem. Commun. 2013, 49, 5307; (e) Yuan, L.
H.; Zeng, H. Q.; Yamato, K.; Sanford, A. R.; Feng, W.; Atreya, H. S.;
Sukumaran, D. K.; Szyperski, T.; Gong, B. J. Am. Chem. Soc. 2004,
126, 16528; (f) Feng, W.; Yamato, K.; Yang, L. Q.; Ferguson, J. S.;
Zhong, L. J.; Zou, S. L.; Yuan, L. H.; Zeng, X. C.; Gong, B. J. Am.
Chem. Soc. 2009, 131, 2629.
[7] (a) Wu, X. X.; Liang, G. X.; Ji, G.; Fun, H.-K.; He, L.; Gong, B.
Chem. Commun. 2012, 48, 2228; (b) Hu, J. C.; Chen, L.; Ren, Y.;
Deng, P. C.; Li, X. W.; Wang, Y. J.; Jia, Y. M.; Luo, J.; Yang, X. S.;
Feng, W.; Yuan, L. H. Org. Lett. 2013, 15, 4670; (c) Chen, L.; Peng,
Z. Y.; Liu, S.; Feng, W.; Yuan, L. H. Org. Lett. 2015, 17, 5950; (d)
Shi, S. S.; Zhu, Y. M.; Li, X. W.; Yuan, X. Y.; Ma, T.; Yuan, W.-L.;
Tao, G.-H.; Feng, W.; Yuan, L. H. RSC Adv. 2016, 6, 39839.
[8] (a) Gale, P. A.; García-Garrido, S. E.; Garric, J. Chem. Soc. Rev.
2008, 37, 151; (b) Sessler, J. L.; Gale, P. A.; Cho, W.-S. Anion
Receptor Chemistry, Royal Society of Chemistry, Cambridge, UK,
2006; (c) Steed, J. W. Chem. Commun. 2006, 25, 2637; (d) Davis, A.
P. Coord. Chem. Rev. 2006, 250, 2939; (e) Gale, P. A. Acc. Chem.
Res. 2006, 39, 465; (f) Schmidtchen, F. P. Coord. Chem. Rev. 2006,
250, 2918; (g) Gunnlaugsson, T.; Glynn, M.; Hussey, G. M.; Kruger,
P. E.; Pfeffer, F. M. Coord. Chem. Rev. 2006, 250, 3094; (h) Beer, P.
D.; Hayes, E. J. Coord. Chem. Rev. 2003, 240, 167; (i) Kubik, S.
Chem. Soc. Rev. 2009, 38, 585; (j) Kang, S. O.; Hossain, M. A.;
Bowman-James, K. Coord. Chem. Rev. 2006, 250, 3038.
Figure 4 Job’s plot for the complexation of 3 and TBACl in
CDCl3 based on the absorbance at 360 nm, indicating a 1∶1
stoichiometry. The total concentration is 1.2×103 mol/L.
Conclusions
In summary, we demonstrated the effect of local and
entire rigidification of molecular framework imposed by
interior and exterior H-bonding in receptors 1－4 upon
the selective binding of halide anions. The binding af-
finity is strongly dependent on the extent of rigidifica-
tion, saturation of H-bonds and steric hindrance. Results
from the recognition of three halide anions (Cl, Br, I)
are rationalized according to the preferential confor-
mations of receptor molecules. Particularly, single-
crystal X-ray diffraction analysis of trimeric amide 3
provides the molecular conformation that is desired for
efficient association of anions. The information re-
trieved from the present study underscores the im-
portance of H-bonding in effecting the recognition pro-
cess, especially the delicate interplay between the bind-
ing affinity and the molecular structures associated with
intramolecular H-bonds.
Acknowledgement
[9] Kavallieratos, K.; Bertao, C. M.; Crabtree, R. H. J. Org. Chem. 1999,
64, 1675.
[10] (a) Chmielewski, M. J.; Zielinski, T.; Jurczak, J. Pure Appl. Chem.
2007, 79, 1087; (b) Evans, L. S.; Gale, P. A.; Light, M. E.; Quesada,
R. Chem. Commun. 2006, 9, 965; (c) Brooks, S. J.; Edwards, P. R.;
Gale, P. A.; Light, M. E. New J. Chem. 2006, 30, 65.
The authors acknowledge the National Natural Sci-
ence Foundation of China (No. 21572143) and Open
Project of State Key Laboratory of Supramolecular
Structure and Material (No. SKLSSM201629) for fund-
ing this work. The Comprehensive Training Platform of
[11] (a) Wei, L.-H.; He, Y.-B.; Wu, J.-L.; Qin, H.-J.; Xu, K.-X.; Meng,
6
www.cjc.wiley-vch.de
© 2016 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2016, XX, 1—7

Effect of Hydrogen Binding on Selective Recognition of Halide Anions
L.-Z. Chin. J. Chem. 2005, 23, 608; (b) Wei, W.; Zhang, Y.-M.; Wei,
T.-B. Chin. J. Chem. 2008, 26, 1935; (c) Zhang, Y.-M.; Cao, C.; Wei,
W.; Xie, T.-B. Chin. J. Chem. 2007, 25, 709; (d) Liu, Y.-Z.; Yuan, K.;
Yuan, Z.; Zhu, Y.-C.; Lv, L.-L. RSC Adv. 2016, 6, 14666; (e) Canard,
G.; Edzang, J. A.; Chen, Z.; Chessé, M.; Elhabiri, M.; Giorgi, M.;
Siri, O. Chem. Eur. J. 2016, 22, 5756.
[17] Li, Y.; Jia, Y. M.; Wang, Z. W.; Li, X. H.; Feng, W.; Deng, P. C.;
Yuan, L. H. RSC Adv. 2014, 4, 29702.
[18] Chu, H. Z.; He, L. T.; Jiang, Q.; Fang, Y. Y.; Jia, Y. M.; Yuan, X. Y.;
Zou, S. L.; Li, X. H.; Feng, W.; Yang, Y. Y.; Liu, N.; Luo, S. Z.;
Yang, Y. Q.; Yang, L.; Yuan, L. H. J. Hazard. Mater. 2014, 264, 211.
[19] Alyapyshev, M. Y.; Babain, V. A.; Tkachenko, L. I.; Eliseev, I. I.;
Didenko, A. V.; Petrov, M. L. Sol. Extr. Ion Exch. 2011, 29, 619.
[20] Kavallieratos, K.; Gala, S. R.; Austin, D. J.; Crabtree, R. H. J. Am.
Chem. Soc. 1997, 119, 2325.
[12] Hughes, M. P.; Smith, B. D. J. Org. Chem. 1997, 62, 4492.
[13] Alejandro, D.-G.; Höpfl, H.; Medrano, F.; Yatsimirsky, A. K. J. Org.
Chem. 2010, 75, 2259.
[14] Santacroce, P. V.; Davis, J. T.; Light, M. E.; Gale, P. A.;
Iglesias-Sánchez, J. C.; Prados, P.; Quesada, R. J. Am. Chem. Soc.
2007, 129, 1886.
[21] Bisson, A. P.; Carver, F. J.; Eggleston, D. S.; Haltiwanger, R. C.;
Hunter, C. A.; Livingstone, D. L.; McCabe, J. F.; Rotger, C.; Rowan,
A. E. J. Am. Chem. Soc. 2000, 122, 8856.
[15] Chen, L.; Yuan, X. Y.; Wang, Z. X.; Luo, Y. R.; Huang, W.; Zhang,
S.; Yuan, W. L.; Qin, S.; Tao, G. Z.; Yuan, L. H. Asian J. Org. Chem.
2016, DOI: 10.1002/ajoc.201600161.
[22] Thordarson, P. Chem. Soc. Rev. 2011, 40, 1305.
[23] (a) Gao, R. Z.; Hu, J. C.; Zhang, K.; He, Y. Z.; Liu, P.; Luo, S. Z.;
Yang, Y. Q.; Yang, L.; Feng, W.; Yuan, L. H. Chin. J. Chem. 2013,
31, 689; (b) He, L. T.; Jiang, Q.; Gao, R. Z.; Yang, X. S.; Feng, W.;
Luo, S. Z.; Yang, Y. Q.; Yang, L.; Yuan, L. H. Sci China Chem. 2014,
57, 1246.
[24] Yang, Q. Y.; Zhou, Z. Y.; Qi, J. Y. Acta Cryst. 2001, E57, o1161.
[25] Wang, Q.-Q.; Begum, R. A.; Day, V. W.; Bowman-James, K. J. Am.
Chem. Soc. 2013, 135, 17193.
[26] CCDC 1474918 (3) contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge from
The Cambridge Crystallographic Data Centre.
[27] (a) Hunter, C. A.; Purvis, D. H. Angew. Chem., Int. Ed. Engl. 1992,
31, 792; (b) Chmielewski, M. J.; Jurczak, J. Chem. Eur. J. 2006, 12,
7652.
[16] (a) Yang, Y. A.; Feng, W.; Hu, J. H.; Zou, S. L.; Gao, R. Z.; Yamato,
K.; Kline, M.; Cai, Z. H.; Gao, Y.; Wang, Y. B.; Li, Y. B.; Yang, Y. L.;
Yuan, L. H.; Zeng, X. C.; Gong, B. J. Am. Chem. Soc. 2011, 133,
18590; (b) Wu, L.; Fang, Y. Y.; Jia, Y. M.; Yang, Y. Y.; Liao, J. L.;
Liu, N.; Yang, X. S.; Feng, W.; Ming, J. L.; Yuan, L. H. Dalton
Trans. 2014, 43, 3835; (c) Fang, Y. Y.; Wu, L.; Liao, J. L.; Chen, L.;
Yang, Y. Y.; Liu, N.; He, L. T.; Zou, S. L.; Feng, W.; Yuan, L. H.
RSC Adv. 2013, 3, 12376; (d) Yang, X. S.; Chen, L.; Yang, Y. A.; He,
Y. Z.; Zou, S. L.; Feng, W.; Yang, Y. Y.; Liu, N.; Liao, J. L.; Yuan, L.
H. J. Hazard. Mater. 2012, 217, 171; (e) Jia, Y. M.; Fang, Y. Y.; Li,
Y.; He, L. T.; Fan, W. H.; Feng, W.; Yang, Y. Y.; Liao, J. L.; Liu, N.;
Yuan, L. H. Talanta 2014, 125, 322; (f) He, L. T.; Jiang, Q.; Jia, Y.
M.; Fang, Y. Y.; Zou, S. L.; Yang, Y. Y.; Liao, J. L.; Liu, N.; Feng, W.;
Luo, S. Z.; Yang, Y. Q.; Yang, L.; Yuan, L. H. J. Chem. Technol.
Biotechnol. 2013, 88, 1930.
[28] Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond in Structural
Chemistry and Biology, Oxford University Press, New York, 1999,
pp. 29－121.
(Cheng, F.)
Chin. J. Chem. 2016, XX, 1—7
© 2016 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cjc.wiley-vch.de
7