210
N. Tshilande and L. Mammino
by acronyms on reporting and analysing results: HF for HF/6-31G(d,p), DFT for
DFT/B3LYP/6-31+G(d,p) and MP2 for MP2/6-31G(d,p) for the calculation methods;
‘vac’, ‘chlrf’, ‘actn’ and ‘aq’ respectively for vacuum, chloroform, acetonitrile and
water.
Besides the tables and figures included in the text, expanded tables and figures
(showing the relevant images and the values of relevant properties for all the calculated conformers), as well as comparative tables, and figures with comparative
graphs for the data for which trend-comparisons can be visualised, are provided in
the Electronic Supplementary Information (ESI). They may be cited in this text, and
their numbers are preceded by an S. The ESI figures are organised in such a way
that all the figures showing images (conformers or molecular orbitals, Figs. S1–S16)
precede the set of figures showing trends’ comparisons (Figs. S17–S132). The scales
of the comparative diagrams are selected for each diagram, to better fit the values
considered.
3 Calculations and Results
3.1 Naming of Conformers
Conformers are denoted with acronyms providing information on their characteristics. The same letters that had been used to keep track of relevant geometry features
of ACPLs [10–21] are here used for the conformers of MYRA and DBPO, with
some additional letters for features specific to these molecules. All the letters and
their meanings are listed in Table 1. On presenting the analysis of results, it is also
important to be able to mention each ring individually; thus, the rings are denoted
by uppercase letters (A, B, D, E) as shown in Fig. 2. Although the substituent may
collectively be called R
(Fig. 1), it is termed ‘BDE ring system’, or simply ‘BDE’,
when it is relevant to recall that it consists of three rings. The two fused rings are
comprehensively termed ‘BD ring system’ or simply BD. The system comprising
all the rings (including the phloroglucinol moiety) is termed ‘ABDE ring system’ or
simply ‘ABDE’.
The following features are taken into consideration when naming the conformers:
the first IHB (whether H15···O14 or H17···O14); the O–H···π IHB (whether H15···π
or H16···π); the orientation of O10–H16; the orientation of the phenol OH ortho to
CRO and not engaged in the first IHB; the orientation of the BDE ring system with
respect to the A moiety; the orientation of O28–H29; the orientation of O36–H37;
the position of C19 with respect to the plane identified by C9, C23, C22 and O21 (to
be considered because ring D is not planar); the angle by which the specified single
bond in R is rotated with respect to the linear geometry, at input level, to generate
new conformers having different geometries of R (Fig. 3 shows the numbers by
which the single bonds of R are concisely denoted in the acronyms). For instance,
MYRA-d-r-η-p-a-e-j is a conformer of MYRA in which the first IHB is on the same
N. Tshilande and L. Mammino
by acronyms on reporting and analysing results: HF for HF/6-31G(d,p), DFT for
DFT/B3LYP/6-31+G(d,p) and MP2 for MP2/6-31G(d,p) for the calculation methods;
‘vac’, ‘chlrf’, ‘actn’ and ‘aq’ respectively for vacuum, chloroform, acetonitrile and
water.
Besides the tables and figures included in the text, expanded tables and figures
(showing the relevant images and the values of relevant properties for all the calculated conformers), as well as comparative tables, and figures with comparative
graphs for the data for which trend-comparisons can be visualised, are provided in
the Electronic Supplementary Information (ESI). They may be cited in this text, and
their numbers are preceded by an S. The ESI figures are organised in such a way
that all the figures showing images (conformers or molecular orbitals, Figs. S1–S16)
precede the set of figures showing trends’ comparisons (Figs. S17–S132). The scales
of the comparative diagrams are selected for each diagram, to better fit the values
considered.
3 Calculations and Results
3.1 Naming of Conformers
Conformers are denoted with acronyms providing information on their characteristics. The same letters that had been used to keep track of relevant geometry features
of ACPLs [10–21] are here used for the conformers of MYRA and DBPO, with
some additional letters for features specific to these molecules. All the letters and
their meanings are listed in Table 1. On presenting the analysis of results, it is also
important to be able to mention each ring individually; thus, the rings are denoted
by uppercase letters (A, B, D, E) as shown in Fig. 2. Although the substituent may
collectively be called R
(Fig. 1), it is termed ‘BDE ring system’, or simply ‘BDE’,
when it is relevant to recall that it consists of three rings. The two fused rings are
comprehensively termed ‘BD ring system’ or simply BD. The system comprising
all the rings (including the phloroglucinol moiety) is termed ‘ABDE ring system’ or
simply ‘ABDE’.
The following features are taken into consideration when naming the conformers:
the first IHB (whether H15···O14 or H17···O14); the O–H···π IHB (whether H15···π
or H16···π); the orientation of O10–H16; the orientation of the phenol OH ortho to
CRO and not engaged in the first IHB; the orientation of the BDE ring system with
respect to the A moiety; the orientation of O28–H29; the orientation of O36–H37;
the position of C19 with respect to the plane identified by C9, C23, C22 and O21 (to
be considered because ring D is not planar); the angle by which the specified single
bond in R is rotated with respect to the linear geometry, at input level, to generate
new conformers having different geometries of R (Fig. 3 shows the numbers by
which the single bonds of R are concisely denoted in the acronyms). For instance,
MYRA-d-r-η-p-a-e-j is a conformer of MYRA in which the first IHB is on the same